Water → HCID 53374175, compound

HRID 869692Notes

Reaction equation

ClC1N=[C:6]([NH:8][CH2:9][C:10]([CH3:13])([OH:12])[CH3:11])[N:5]2[N:14]=[C:15]([C:17]3[C:26]([CH3:27])=[N:25][C:24]4[C:19](=[CH:20][C:21]([F:28])=[CH:22][CH:23]=4)[N:18]=3)[CH:16]=[C:4]2C=1.Cl.[F:30][C@@H:31]1[CH2:35][CH2:34][NH:33][CH2:32]1.[N:36]12CCCN=C1CCC[CH2:38][CH2:37]2.O>CN1CCCC1=O>[F:28][C:21]1[CH:20]=[C:19]2[C:24]([N:25]=[C:26]([CH3:27])[C:17]([C:15]3[CH:16]=[C:4]4[N:36]=[C:37]([N:33]5[CH2:34][CH2:35][C@@H:31]([F:30])[CH2:32]5)[CH:38]=[C:6]([NH:8][CH2:9][C:10]([CH3:11])([OH:12])[CH3:13])[N:5]4[N:14]=3)=[N:18]2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of 1-{[5-chloro-2-(7-fluoro-3-methylquinoxalin-2-yl)pyrazolo[1,5-c]pyrimidin-7-yl]amino}-2-methylpropan-2-ol (170 mg, 0.424 mmol), (R)-3-fluoropyrrolidine hydrochloride (268 mg, 2.12 mmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (387 mg, 2.54 mmol) in N-methylpyrrolidinone (5.0 mL) was heated at 70° C. overnight. After being cooled to ambient temperature, the reaction mixture was diluted with ice-cooled water. The resulting precipitate was collected and washed with water to give 1-({2-(7-fluoro-3-methylquinoxalin-2-yl)-5-[(3R)-3-fluoropyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-7-yl}amino)-2-methylpropan-2-ol. MS (APCI): m/z 454 (M+H).

Workup

temperatureAfter being cooled to ambient temperature
additionthe reaction mixture was diluted with ice-
customThe resulting precipitate was collected
washwashed with water

Sources & evidence

ORD record: ord-09dcb951b3b848c49b2c56de1c2d7901
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969376B2

Reaction notes

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