2-(Thiazol-2-yl)but-3-yn-2-ol → 4-[1-(2-aminopyrimidin-4-yl)-3-[(pyrrolidin-1-yl)carbonyl]-1H-indazol-6-yl]-2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol

HRID 1398575Notes

Reaction equation

HRID 1398575 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:18]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:19])=[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.S1C=CN=C1C(O)(C#C)C.[CH3:35][C:36]1[O:40][N:39]=[C:38]([C:41]([OH:45])([C:43]#[CH:44])[CH3:42])[CH:37]=1>>[NH2:17][C:13]1[N:12]=[C:11]([N:8]2[C:9]3[C:5](=[CH:4][CH:3]=[C:2]([C:44]#[C:43][C:41]([C:38]4[CH:37]=[C:36]([CH3:35])[O:40][N:39]=4)([OH:45])[CH3:42])[CH:10]=3)[C:6]([C:18]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:19])=[N:7]2)[CH:16]=[CH:15][N:14]=1

Participants

4

Reactant 3

HCID 582215512-(Thiazol-2-yl)but-3-yn-2-olHCID 582217592-(5-Methylisoxazol-3-yl)but-3-yn-2-olHCID 681815664-{6-Bromo-3-[(pyrrolidin-1-yl)carbonyl]indazol-1-yl}pyrimidin-2-amine

Product 1

HCID 601646334-[1-(2-aminopyrimidin-4-yl)-3-[(pyrrolidin-1-yl)carbonyl]-1H-indazol-6-yl]-2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol

Procedure

The title compound was prepared by procedure described in Example 62-c, by substituting 1-(2-aminopyrimidin-4-yl)-6-bromo-N,N-dimethylindazole-3-carboxamide with 4-{6-bromo-3-[(pyrrolidin-1-yl)carbonyl]indazol-1-yl}pyrimidin-2-amine and 2-(1,3-thiazol-2-yl)but-3-yn-2-ol with 2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol in Step 3: 1H NMR (500 MHz, DMSO) delta 1.84-1.93 (5H, m), 1.93-1.98 (2H, m), 2.42 (3H, s), 3.60 (2H, t, J=6.86 Hz), 3.99 (2H, t, J=6.78 Hz), 6.41 (1H, s), 6.57 (1H, s), 7.13 (1H, d, J=5.36 Hz), 7.15 (2H, br. s.), 7.44 (1H, dd, J=8.43, 1.18 Hz), 8.22 (1H, d, J=8.35 Hz), 8.36 (1H, d, J=5.52 Hz), 8.94 (1H, s); LC-MS: m/z=+458.45 (M+H)+.

Sources & evidence

ORD record
ord-531bad743cf04b98929f3fddd8685854
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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