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

HRID 1398574Notes

Reaction equation

HRID 1398574 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:18]([N:20]3[CH2:25][CH2:24][O: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.[CH3:36][C:37]1[O:41][N:40]=[C:39]([C:42]([OH:46])([C:44]#[CH:45])[CH3:43])[CH:38]=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:45]#[C:44][C:42]([C:39]4[CH:38]=[C:37]([CH3:36])[O:41][N:40]=4)([OH:46])[CH3:43])[CH:10]=3)[C:6]([C:18]([N:20]3[CH2:25][CH2:24][O: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 681816314-{6-Bromo-3-[(morpholin-4-yl)carbonyl]indazol-1-yl}pyrimidin-2-amine

Product 1

HCID 601646324-[1-(2-aminopyrimidin-4-yl)-3-[(morpholin-4-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 61-c, by substituting 1-(2-aminopyrimidin-4-yl)-6-bromo-N,N-dimethylindazole-3-carboxamide with 4-{6-bromo-3-[(morpholin-4-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 1.86 (3H, s), 2.42 (3H, s), 3.63-3.70 (2H, m), 3.70-3.80 (4H, m), 3.89-3.97 (2H, m), 6.41 (1H, s), 6.58 (1H, s), 7.08 (1H, d, J=5.36 Hz), 7.16 (2H, br. s.), 7.44 (1H, dd, J=8.35, 1.26 Hz), 8.02 (1H, d, J=8.35 Hz), 8.35 (1H, d, J=5.36 Hz), 8.94 (1H, s); LC-MS: m/z=+474.4 (M+H)+.

Sources & evidence

ORD record
ord-e4ec0c51b1ee4a9690dd26c1feec7cad
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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