Allyl bromide → HCID 57526825, compound

HRID 1452636Notes

Reaction equation

O1C[CH2:4][CH2:3][CH2:2]1.[CH2:6]([C:9]1[C:10]([NH:35][C@H:36]2[CH2:41][CH2:40][CH2:39][N:38]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:37]2)=[N:11][C:12]2[N:13]([N:32]=[CH:33][CH:34]=2)[C:14]=1[N:15]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[CH:18][CH:17]=1)[CH:7]=[CH2:8].[H-].[Na+].C(Br)C=C>O.CN(C)C=O>[CH2:4]([N:35]([C:10]1[C:9]([CH2:6][CH:7]=[CH2:8])=[C:14]([N:15]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH3:24])=[CH:20][CH:21]=2)[N:13]2[N:32]=[CH:33][CH:34]=[C:12]2[N:11]=1)[C@H:36]1[CH2:41][CH2:40][CH2:39][N:38]([C:42]([O:44][C:45]([CH3:47])([CH3:46])[CH3:48])=[O:43])[CH2:37]1)[CH:3]=[CH2:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixed solution of tetrahydrofuran (0.6 mL) and N,N-dimethylformamide containing tert-butyl (S)-3-{6-allyl-7-[tert-butoxycarbonyl-(4-ethoxyphenyl)amino]pyrazolo[1,5-a]pyrimidin-5-ylamino}piperidine-1-carboxylate (100 mg, 0.168 mmol), sodium hydride and allyl bromide were added at 0° C., and the mixture was stirred at 70° C. for 5 hr. To the reaction solution, water was added, and the mixture was extracted with ethyl acetate. The combined ethyl acetate layer was dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was distilled off to obtain the title compound (102 mg).

Workup

additionwere added at 0° C.
extractionthe mixture was extracted with ethyl acetate
dry with materialThe combined ethyl acetate layer was dried over sodium sulfate
filtrationAfter the sodium sulfate was filtered off
distillationthe solvent was distilled off

Sources & evidence

ORD record: ord-6863790bbc7f434d80ce3229a1cec710
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473694B2

Reaction notes

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