Diisopropylethylamine → 1-(7-Amino-5-(1-(morpholinosulfonyl)piperidin-4-yl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone

HRID 2047184Notes

Reaction equation

CCN(C(C)C)C(C)C.[NH2:10][C:11]1[N:16]2[N:17]=[CH:18][C:19]([C:20]3[CH:21]=[N:22][C:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:24][CH:25]=3)=[C:15]2[N:14]=[C:13]([CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[C:12]=1[C:38](=[O:40])[CH3:39].[N:41]1([S:47](Cl)(=[O:49])=[O:48])[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1>CN(C=O)C>[NH2:10][C:11]1[N:16]2[N:17]=[CH:18][C:19]([C:20]3[CH:21]=[N:22][C:23]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)=[CH:24][CH:25]=3)=[C:15]2[N:14]=[C:13]([CH:32]2[CH2:33][CH2:34][N:35]([S:47]([N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)(=[O:49])=[O:48])[CH2:36][CH2:37]2)[C:12]=1[C:38](=[O:40])[CH3:39]

Participants

Conditions

Temperature: 0 °C

Procedure

DIEA (121 mg, 0.94 mmoL) was added to at 0° C. a mixture of 1-(7-amino-3-(6-phenylpyridin-3-yl)-5-(piperidin-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone (64.3 mg, 0.15 mmoL) and morpholine-4-sulfonyl chloride (28.9 mg, 0.15 mmol) in DMF (3 mL). After stirring at 0° C. for 0.5 h and then room temperature for 2 h, the mixture was purified by prep-LC to afford 1-(7-amino-5-(1-(morpholinosulfonyl)piperidin-4-yl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone, LCMS tR=3.83 Min (5 min run, UV254nm). Mass calculated for, M+ 561.66, observed LC/MS m/z 567.66 (M+H).

Workup

waitroom temperature for 2 h
customthe mixture was purified by prep-LC

Sources & evidence

ORD record: ord-4ad1c1a66dd443e4a6ccbf85402e6f57
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08591943B2

Reaction notes

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