2-(Cyanomethyl)-1,3-thiazole-4-carboxylic acid → (R)-N-(2-(3-(4-cyano-3,5-difluorophenyl)-1H-pyrazol-1-yl)propyl)-2-(cyanomethyl)thiazole-4-carboxamide

HRID 872753Notes

Reaction equation

HRID 872753 reaction equation
[NH2:1][CH2:2][C@H:3]([N:5]1[CH:9]=[CH:8][C:7]([C:10]2[CH:17]=[C:16]([F:18])[C:13]([C:14]#[N:15])=[C:12]([F:19])[CH:11]=2)=[N:6]1)[CH3:4].[C:20]([CH2:22][C:23]1[S:24][CH:25]=[C:26]([C:28](O)=[O:29])[N:27]=1)#[N:21]>>[C:14]([C:13]1[C:16]([F:18])=[CH:17][C:10]([C:7]2[CH:8]=[CH:9][N:5]([C@H:3]([CH3:4])[CH2:2][NH:1][C:28]([C:26]3[N:27]=[C:23]([CH2:22][C:20]#[N:21])[S:24][CH:25]=3)=[O:29])[N:6]=2)=[CH:11][C:12]=1[F:19])#[N:15]

Participants

3

Reactant 2

HCID 431403362-(Cyanomethyl)-1,3-thiazole-4-carboxylic acidHCID 67172435(R)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2,6-difluorobenzonitrile

Product 1

HCID 67171219(R)-N-(2-(3-(4-cyano-3,5-difluorophenyl)-1H-pyrazol-1-yl)propyl)-2-(cyanomethyl)thiazole-4-carboxamide

Procedure

The title compound was prepared from (R)-4-(1-(1-aminopropan-2-yl)-1H-pyrazol-3-yl)-2,6-difluorobenzonitrile (380 mg, 1.45 mmol) and 2-(cyanomethyl)-thiazole-4-carboxylic acid (244 mg, 1.45 mmol) using the method of Example 34(d). Yield 70 mg. 1H NMR (400 MHz; d6-DMSO): δ 1.47 (d, 3H), 3.29 (s, 2H), 3.67 (m, 2H), 4.74 (m, 1H), 6.99 (d, 1H), 7.77 (m, 2H), 7.92 (d, 1H), 8.25 (d, 1H), 8.44 (m, 1H).

Sources & evidence

ORD record
ord-1c9003d159da46d79f82c795adacd268
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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