(R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-ol → 1-(2-aminopyrimidin-4-yl)-6-[(3R)-3-hydroxy-3-(5-methyl-1,2-oxazol-3-yl)but-1-yn-1-yl]-1H-indazole-3-carboxamide

HRID 1398579Notes

Reaction equation

HRID 1398579 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=3)[C:10]([C:18]([NH2:20])=[O:19])=[N:9]2)[CH:5]=[CH:4][N:3]=1.[CH3:21][C:22]1[O:26][N:25]=[C:24]([C@:27]([OH:31])([C:29]#[CH:30])[CH3:28])[CH:23]=1>>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:30]#[C:29][C@@:27]([OH:31])([C:24]4[CH:23]=[C:22]([CH3:21])[O:26][N:25]=4)[CH3:28])[CH:15]=3)[C:10]([C:18]([NH2:20])=[O:19])=[N:9]2)[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 58221468(R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-olHCID 681816251-(2-Aminopyrimidin-4-yl)-6-bromoindazole-3-carboxamide

Product 1

HCID 601650451-(2-aminopyrimidin-4-yl)-6-[(3R)-3-hydroxy-3-(5-methyl-1,2-oxazol-3-yl)but-1-yn-1-yl]-1H-indazole-3-carboxamide

Procedure

The title compound was prepared by procedure as described in Example 62-c by reacting 1-(2-aminopyrimidin-4-yl)-6-bromoindazole-3-carboxamide and (2R)-2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol: 1H NMR (500 MHz, DMSO) delta 1.86 (3H, s), 2.42 (3H, s), 6.41 (1H, s), 6.59 (1H, s), 7.16 (2H, br. s.), 7.34 (1H, d, J=5.52 Hz), 7.44 (1H, dd, J=8.43, 1.18 Hz), 7.75 (1H, s), 8.21 (1H, s), 8.26 (1H, d, J=8.35 Hz), 8.38 (1H, d, J=5.52 Hz), 8.93 (1H, s); LC-MS: m/z=+404 (M+H)+.

Sources & evidence

ORD record
ord-bf12e179c4884716b66378592274b1c5
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

Loading…