N-bromobutanimide → HCID 66733274, compound

HRID 2047164Notes

Reaction equation

HRID 2047164 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[O:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[C:19]([N:21]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[N:18]3[N:38]=[CH:39][C:40]([C:41]4[CH:42]=[N:43][C:44]5[C:49]([CH:50]=4)=[CH:48][CH:47]=[CH:46][CH:45]=5)=[C:17]3[N:16]=2)[CH2:11][CH2:10]1>CC#N>[Br:8][C:20]1[C:15]([N:12]2[CH2:11][CH2:10][O:9][CH2:14][CH2:13]2)=[N:16][C:17]2[N:18]([N:38]=[CH:39][C:40]=2[C:41]2[CH:42]=[N:43][C:44]3[C:49]([CH:50]=2)=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:19]=1[N:21]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:35])([CH3:36])[CH3:37])[CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66733517HCID 66733517, compound

Product 1

HCID 66733274HCID 66733274, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of NBS (20.6 mg, 0.116 mmoL) in CH3CN (1 mL) was added to a mixture of 5-morpholino-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (70.0 mg, 0.116 mmoL) in CH3CN (6 mL). After stirring at room temperature for 10 min, the reaction mixture was concentrated and purified by column chromatography to afford 6-bromo-5-morpholino-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine. LCMS tR=2.91 Min (5 min run, UV254nm). Mass calculated for, M+ 684.2, observed LC/MS m/z 685.2 (M+H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-ace7c5a160284ddba11c72a14ee7635b
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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