HCID 68182595、化合物 → HCID 178522357、化合物

HRID 1623935ノート

反応式

HRID 1623935 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:16]2[C@@H:15]3[CH2:17][C@@H:14]3[CH2:13][C:12]=2[C:11]([C:18](O)=[O:19])=[N:10]1.[NH2:21][C:22]1[CH:27]=[C:26]([OH:28])[CH:25]=[CH:24][N:23]=1>>[OH:28][C:26]1[CH:25]=[CH:24][N:23]=[C:22]([NH:21][C:18]([C:11]2[C:12]3[CH2:13][C@H:14]4[CH2:17][C@H:15]4[C:16]=3[N:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])[N:10]=2)=[O:19])[CH:27]=1

参加物

3

反応物 2

HCID 68182595HCID 68182595、化合物HCID 178507942HCID 178507942、化合物

生成物 1

HCID 178522357HCID 178522357、化合物

実験手順

A solution of 4-methoxypyridin-2-amine (100 mg, 0.806 mmol) in DCM (1.6 mL) under N2 atmosphere was cooled in an dry ice/IPA bath, and tribromoborane (0.305 mL, 3.23 mmol) was added with a syringe. After removing the cold bath, the reaction was stirred overnight at room temperature. The reaction mixture was diluted with water (5 mL) and stirred for an additional 30 min. It was then washed with saturated NaHCO3 (20 mL) to pH=7 and extracted with DCM (3×20 mL). The combined organic layer was dried over MgSO4 and concentrated to provide 2-aminopyridin-4-ol. The title compound was prepared in a manner similar to that described in Method EE using Intermediate 1 (see Example 1.1) and 2-aminopyridin-4-ol. LCMS m/z=369.3 [M+H]+; 1H NMR: (400 MHz, CD3CN) δ ppm 0.50 (td, J=4.7 and 3.5 Hz, 1H), 1.22 (td, J=7.8 and 4.9 Hz, 1H), 2.21-2.26 (m, 1H), 2.31-2.38 (m, 1H), 2.93 (d, J=16.7 Hz, 1H), 3.05 (dd, J=16.6 and 6.3 Hz, 1H), 6.80 (dd, J=7.1 and 2.2 Hz, 1H), 6.95 (d, J=2.2 Hz, 1H), 7.15-7.21 (m, 1H), 7.22-7.29 (m, 1H), 7.52 (s, 1H), 7.70 (td, J=8.8 and 5.9 Hz, 1H), 7.82 (d, J=7.1 Hz, 1H).

出典と根拠

ORDレコード
ord-7bda950a0a6b44d58bd7862c79f6905a
出典データセット
uspto-grants-2014_07
特許番号
US08778950B2

反応ノート

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