2-Methyl-3-butyn-2-ol → HCID 68181720, compound

HRID 1398568Notes

Reaction equation

HRID 1398568 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:18][N:19]3[CH2:22][C:21]([F:24])([F:23])[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.[CH3:31][C:32]1[O:36][N:35]=[C:34]([C@:37]([OH:41])([C:39]#[CH:40])[CH3:38])[N:33]=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:40]#[C:39][C@:37]([C:34]4[N:33]=[C:32]([CH3:31])[O:36][N:35]=4)([OH:41])[CH3:38])[CH:10]=3)[C:6]([CH2:18][N:19]3[CH2:22][C:21]([F:24])([F:23])[CH2:20]3)=[N:7]2)[CH:16]=[CH:15][N:14]=1

Participants

4

Reactant 3

HCID 82582-Methyl-3-butyn-2-olHCID 68181922HCID 68181922, compoundHCID 86669593(R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)but-3-yn-2-ol

Product 1

HCID 68181720HCID 68181720, compound

Procedure

The title compound was prepared by the procedure described in Example 10-c by substituting 4-{6-bromo-3-[(dimethylamino)methyl]-1H-indazol-1-yl}pyrimidin-2-amine with of 4-{6-bromo-3-[(3,3-difluoroazetidin-1-yl)methyl]indazol-1-yl}pyrimidin-2-amine and 2-methyl-but-3-yn-2-ol with (2R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)but-3-yn-2-ol: 1H NMR (500 MHz, CDCl3) delta 2.09 (3H, s), 2.67 (3H, s), 3.73 (4H, t, J=12.06 Hz), 4.12 (2H, s), 4.80-5.13 (1 H, m), 5.51 (2H, s), 7.28 (1H, d, J=5.67 Hz), 7.37 (1H, dd, J=8.28, 1.02 Hz), 7.79 (1H, d, J=8.20 Hz), 8.30 (1H, d, J=5.67 Hz), 8.86 (1H, s); LC-MS: m/z=+467.1 (M+H)+.

Sources & evidence

ORD record
ord-3ab71534ada248478810ce7af32da7ff
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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