Tetrahydrofuran → HCID 58431363, compound

HRID 1617359Notes

Reaction equation

Cl.Cl.Cl.[CH3:4][Si:5]([CH3:32])([CH3:31])[CH2:6][CH2:7][O:8][CH2:9][N:10]1[C:14]2[N:15]=[CH:16][N:17]=[C:18]([C:19]3[CH:20]=[N:21][N:22]([C:24]4([CH2:28][C:29]#[N:30])[CH2:27][NH:26][CH2:25]4)[CH:23]=3)[C:13]=2[CH:12]=[CH:11]1.[CH3:33][N:34]1[C:38]([S:39](Cl)(=[O:41])=[O:40])=[CH:37][CH:36]=[N:35]1.C([N:45]([CH2:48][CH3:49])[CH2:46][CH3:47])C.[CH2:50]1COCC1>>[CH3:33][N:34]1[C:38]([S:39]([N:45]2[CH2:46][CH2:47][CH:50]([N:26]3[CH2:25][C:24]([CH2:28][C:29]#[N:30])([N:22]4[CH:23]=[C:19]([C:18]5[C:13]6[CH:12]=[CH:11][N:10]([CH2:9][O:8][CH2:7][CH2:6][Si:5]([CH3:31])([CH3:4])[CH3:32])[C:14]=6[N:15]=[CH:16][N:17]=5)[CH:20]=[N:21]4)[CH2:27]3)[CH2:49][CH2:48]2)(=[O:41])=[O:40])=[CH:37][CH:36]=[N:35]1

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 224726211-Methyl-1H-pyrazole-5-sulfonyl chloride

HCID 67390808HCID 67390808, compound

Product 1

HCID 58431363HCID 58431363, compound

Procedure

A mixture of {3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile trihydrochloride (44.4 mg, 0.108 mmol), 1-methyl-1H-pyrazole-5-sulfonyl chloride (19.6 mg, 0.108 mmol) and triethylamine (0.0412 mL, 0.296 mmol) in THF (10.0 mL) was stirred at room temperature for 2 hours. Purification on silica gel column afforded the desired product {1-{1-[(1-methyl-1H-pyrazol-5-yl)sulfonyl]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. Yield: 58.8%. LC-MS: 637.3 (M+H)+.

Workup

customPurification on silica gel column

Sources & evidence

ORD record: ord-64d6c77fbc4c47458284db05f6b02c38
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765734B2

Reaction notes

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