N-bromobutanimide → HCID 66980176, compound

HRID 1423323Notes

Reaction equation

HRID 1423323 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][Si:10]([CH3:59])([CH3:58])[CH2:11][CH2:12][O:13][CH2:14][N:15]([CH2:50][O:51][CH2:52][CH2:53][Si:54]([CH3:57])([CH3:56])[CH3:55])[C:16]1[N:21]2[N:22]=[CH:23][C:24]([C:25]3[CH:26]=[N:27][C:28]4[C:33]([CH:34]=3)=[CH:32][C:31]([F:35])=[CH:30][CH:29]=4)=[C:20]2[N:19]=[C:18]([NH:36][CH:37]2[CH2:42][CH2:41][N:40]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:39][CH2:38]2)[CH:17]=1>CC#N.C(Cl)Cl>[CH3:57][Si:54]([CH3:56])([CH3:55])[CH2:53][CH2:52][O:51][CH2:50][N:15]([CH2:14][O:13][CH2:12][CH2:11][Si:10]([CH3:9])([CH3:58])[CH3:59])[C:16]1[N:21]2[N:22]=[CH:23][C:24]([C:25]3[CH:26]=[N:27][C:28]4[C:33]([CH:34]=3)=[CH:32][C:31]([F:35])=[CH:30][CH:29]=4)=[C:20]2[N:19]=[C:18]([NH:36][CH:37]2[CH2:42][CH2:41][N:40]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:39][CH2:38]2)[C:17]=1[Br:8]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 66980260HCID 66980260, compound

Product 1

HCID 66980176HCID 66980176, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

NBS (410.9 mg, 2.31 mmol) was added to a solution of tert-butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-fluoroquinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-ylamino)piperidine-1-carboxylate (1547 mg, 2.09 mmol) in CH3CN (50 mL) and CH2Cl2 (50 mL). After stirring at room temperature for 2 h, the mixture was concentrated in vacuo. Purification by column chromatography afforded tert-butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(6-fluoroquinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-ylamino)piperidine-1-carboxylate: LCMS tR=1.88 Min (5 min run, UV254nm), Mass calculated for M+815.3, observed m/z 816.1 (M+H).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customPurification by column chromatography

Sources & evidence

ORD record
ord-00142e25e73a43ef8814ac9432a8dbf8
Source dataset
uspto-grants-2015_01
Patent number
US08927562B2

Reaction notes

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