4-(Trifluoromethyl)thiazole-2-carboxylic acid → [3-[4-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]-1-(1-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]carbonyl}piperidin-4-yl)azetidin-3-yl]acetonitrile

HRID 1617380Notes

Reaction equation

HRID 1617380 reaction equation
Cl.Cl.Cl.[NH:4]1[CH2:9][CH2:8][CH:7]([N:10]2[CH2:13][C:12]([CH2:36][C:37]#[N:38])([N:14]3[CH:18]=[C:17]([C:19]4[C:20]5[CH:27]=[CH:26][N:25](COCC[Si](C)(C)C)[C:21]=5[N:22]=[CH:23][N:24]=4)[CH:16]=[N:15]3)[CH2:11]2)[CH2:6][CH2:5]1.[F:39][C:40]([F:50])([F:49])[C:41]1[N:42]=[C:43]([C:46](O)=[O:47])[S:44][CH:45]=1>>[N:22]1[C:21]2[NH:25][CH:26]=[CH:27][C:20]=2[C:19]([C:17]2[CH:16]=[N:15][N:14]([C:12]3([CH2:36][C:37]#[N:38])[CH2:13][N:10]([CH:7]4[CH2:8][CH2:9][N:4]([C:46]([C:43]5[S:44][CH:45]=[C:41]([C:40]([F:49])([F:39])[F:50])[N:42]=5)=[O:47])[CH2:5][CH2:6]4)[CH2:11]3)[CH:18]=2)=[N:24][CH:23]=1

Participants

3

Reactant 2

HCID 186730104-(Trifluoromethyl)thiazole-2-carboxylic acidHCID 67391102{1-piperidin-4-yl-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile trihydrochloride

Product 1

HCID 58431379[3-[4-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]-1-(1-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]carbonyl}piperidin-4-yl)azetidin-3-yl]acetonitrile

Procedure

Reaction of {1-piperidin-4-yl-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile trihydrochloride with 4-trifluoromethylthiazol-2-ylcarboxylic acid following the procedure described for Example 1, followed by HPLC purification (method B) provided the title compound. LC-MS: 542.2 (M+H)+.

Workup

  1. customfollowed by HPLC purification (method B)

Sources & evidence

ORD record
ord-47ff72073f96410085f79691dbd607e6
Source dataset
uspto-grants-2014_07
Patent number
US08765734B2

Reaction notes

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