HCID 68182595, compound → HCID 178522357, compound

HRID 1623935Notes

Reaction equation

HRID 1623935 reaction equation
[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

Participants

3

Reactant 2

HCID 68182595HCID 68182595, compoundHCID 178507942HCID 178507942, compound

Product 1

HCID 178522357HCID 178522357, compound

Procedure

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).

Sources & evidence

ORD record
ord-7bda950a0a6b44d58bd7862c79f6905a
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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