(R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-ol → HCID 60164950, compound

HRID 1398577Notes

Reaction equation

HRID 1398577 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]([NH:20][CH3:21])=[O:19])=[N:9]2)[CH:5]=[CH:4][N:3]=1.S1C=CN=C1C(O)(C#C)C.[CH3:32][C:33]1[O:37][N:36]=[C:35]([C@:38]([OH:42])([C:40]#[CH:41])[CH3:39])[CH:34]=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:41]#[C:40][C@@:38]([OH:42])([C:35]4[CH:34]=[C:33]([CH3:32])[O:37][N:36]=4)[CH3:39])[CH:15]=3)[C:10]([C:18]([NH:20][CH3:21])=[O:19])=[N:9]2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 58221468(R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-olHCID 582215512-(Thiazol-2-yl)but-3-yn-2-olHCID 68182019HCID 68182019, compound

Product 1

HCID 60164950HCID 60164950, compound

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 1-(2-aminopyrimidin-4-yl)-6-bromo-N-methylindazole-3-carboxamide and 2-(1,3-thiazol-2-yl)but-3-yn-2-ol with (2R)-2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol in Step 3: 1H NMR (500 MHz, DMSO) delta 1.87 (3H, s), 2.42 (3H, s), 2.87 (3H, d, J=4.73 Hz), 6.42 (1H, s), 6.60 (1H, s), 7.17 (2H, br. s.), 7.32 (1H, d, J=5.36 Hz), 7.46 (1H, dd, J=8.35, 1.10 Hz), 8.27 (1H, d, J=8.20 Hz), 8.40 (1H, d, J=5.36 Hz), 8.78 (1H, d, J=4.73 Hz), 8.94 (1H, s); LC-MS: m/z=+418.05 (M+H)+.

Sources & evidence

ORD record
ord-5ab899d8cd3b4dbabc74734effa62072
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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