2-Methyl-3-butyn-2-ol → 4-[1-(2-aminopyrimidin-4-yl)-3-(morpholin-4-ylmethyl)-1H-indazol-6-yl]-2-(1,3-thiazol-2-yl)but-3-yn-2-ol

HRID 1398486Notes

Reaction equation

HRID 1398486 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[N:7][N:8]2[C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=2)=[CH:4][CH:3]=1.CC(O)(C#C)C.[S:31]1[CH:35]=[CH:34][N:33]=[C:32]1[C:36]([OH:40])([C:38]#[CH:39])[CH3:37]>>[NH2:17][C:13]1[N:12]=[C:11]([N:8]2[C:9]3[C:5](=[CH:4][CH:3]=[C:2]([C:39]#[C:38][C:36]([C:32]4[S:31][CH:35]=[CH:34][N:33]=4)([OH:40])[CH3:37])[CH:10]=3)[C:6]([CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[N:7]2)[CH:16]=[CH:15][N:14]=1

Participants

4

Reactant 3

HCID 82582-Methyl-3-butyn-2-olHCID 582215512-(Thiazol-2-yl)but-3-yn-2-olHCID 681820154-[6-bromo-3-(morpholin-4-ylmethyl)-1H-indazol-1-yl]pyrimidin-2-amine

Product 1

HCID 601640674-[1-(2-aminopyrimidin-4-yl)-3-(morpholin-4-ylmethyl)-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 6-c by substituting 4-{6-bromo-3-[(dimethylamino)methyl]-1H-indazol-1-yl}pyrimidin-2-amine with 4-[6-bromo-3-(morpholin-4-ylmethyl)-1H-indazol-1-yl]pyrimidin-2-amine and 2-methyl-but-3-yn-2-ol with 2-(1,3-thiazol-2-yl)but-3-yn-2-ol. The reaction was carried out at 60° C. for 1.5 hr. Title compound was obtained: 1H NMR (500 MHz, DMSO) δ 1.93 (3H, s), 2.45 (4H, br. s.), 3.55-3.57 (4H, m), 3.88 (2H, s), 6.98 (2H, br. s.), 7.05 (1H, d, J=5.52 Hz), 7.12 (1H, s), 7.35 (1H, dd, J=8.35, 1.26 Hz), 7.68 (1H, d, J=3.31 Hz), 7.78 (1H, d, J=3.31 Hz), 8.01 (1H, d, J=8.35 Hz), 8.27 (1H, d, J=5.52 Hz), 8.87 (1H, s); LC-MS: m/z=+462.1 (M+H)+.

Workup

  1. customThe title compound was prepared by the procedure

Sources & evidence

ORD record
ord-9f258146b5494170834ce38c32dd9f8c
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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