I tried putting my baby down around 9 o'clock, but he was so stubborn he wouldn't go to sleep until midnight.
I tried putting my baby to sleep around 9 p.m., but he was such a tough customer he didn't end up going to sleep until 12 a.m.
ーI tried putting my baby down around 9 o'clock, but he was so stubborn he wouldn't go to sleep until midnight.
「赤ちゃんを９時に寝かせようとしたが、しぶとく12時まで寝なかった」
to put one's baby down で「赤ちゃんを寝かせる」
ーI tried putting my baby to sleep around 9 p.m., but he was such a tough customer he didn't end up going to sleep until 12 a.m.
「赤ちゃんを夜の9時に寝かせようとしたが、しぶとく12時まで寝なかった」
to put one's baby to sleep で「赤ちゃんを寝かせる」
a tough customer で「手強い相手」のことを言います。
ご参考まで！
I was trying to put her/him to sleep at 9 but she/he ended up being awake until 12.
ご質問ありがとうございます。
・「I was trying to put her/him to sleep at 9 but she/he ended up being awake until 12.」
＝彼女/彼を9時くらいに寝かしつけようとしたのですが、結局12時まで起きていました。
（例文）I was trying to put her to sleep at 9 but she ended up being awake until 12. That's why I'm sleep deprived.
（訳）彼女を9時くらいに寝かしつけようとしたのですが、結局12時まで起きていました。そのため、私は寝不足です。
便利な単語：
sleep deprived 寝不足
awake 起きる
お役に立てれば嬉しいです。
Coco
カナダ 
日本 
