(r)-2-(Thiazol-2-yl)but-3-yn-2-ol → (2R)-4-[1-(2-aminopyrimidin-4-yl)-5-fluoro-3-methyl-1H-indazol-6-yl]-2-(1,3-thiazol-2-yl)but-3-yn-2-ol

HRID 1398620Notes

Reaction equation

HRID 1398620 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:18])=[N:7][N:8]2[C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=2)=[CH:4][C:3]=1[F:19].[S:20]1[CH:24]=[CH:23][N:22]=[C:21]1[C@:25]([OH:29])([C:27]#[CH:28])[CH3:26]>>[NH2:17][C:13]1[N:12]=[C:11]([N:8]2[C:9]3[C:5](=[CH:4][C:3]([F:19])=[C:2]([C:28]#[C:27][C@:25]([C:21]4[S:20][CH:24]=[CH:23][N:22]=4)([OH:29])[CH3:26])[CH:10]=3)[C:6]([CH3:18])=[N:7]2)[CH:16]=[CH:15][N:14]=1

Participants

3

Reactant 2

HCID 58221813(r)-2-(Thiazol-2-yl)but-3-yn-2-olHCID 681821964-(6-Bromo-5-fluoro-3-methylindazol-1-yl)pyrimidin-2-amine

Product 1

HCID 68181429(2R)-4-[1-(2-aminopyrimidin-4-yl)-5-fluoro-3-methyl-1H-indazol-6-yl]-2-(1,3-thiazol-2-yl)but-3-yn-2-ol

Procedure

The title compound was prepared by the procedure described in Example 2-b by reacting 4-(6-bromo-5-fluoro-3-methylindazol-1-yl)pyrimidin-2-amine with (2R)-2-(1,3-thiazol-2-yl)but-3-yn-2-ol: 1H NMR (500 MHz, DMSO) delta 1.96 (3H, s), 2.55 (3H, s), 7.02 (3H, s), 7.15 (1H, br. s), 7.71 (1H, d, J=3.15 Hz), 7.79 (1H, s), 7.82 (1H, d, J=8.83 Hz), 8.26 (1H, d, J=5.52 Hz), 8.92 (1H, d, J=6.46 Hz); LC-MS m/z=+395.35 (M+H)+.

Sources & evidence

ORD record
ord-564b8fdeed8c4ffead0f3652c103fe3c
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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