N-bromobutanimide → HCID 66733403, compound

HRID 2047192Notes

Reaction equation

HRID 2047192 reaction equation
C[Si](C)(C)CCOC[N:7](COCC[Si](C)(C)C)[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]([C:27]2[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH:28]=2)[CH:9]=1.[Br:50]N1C(=O)CCC1=O>C(#N)C>[Br:50][C:9]1[C:10]([C:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH:28]=2)=[N:11][C:12]2[N:13]([N:14]=[CH:15][C:16]=2[C:17]2[CH:18]=[N:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:8]=1[NH2:7]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67494206HCID 67494206, compound

Product 1

HCID 66733403HCID 66733403, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-Butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.071 mmol, 50 mg) was charged to a 20 mL scintillation vial containing 1 mL acetonitrile. To this solution was added N-bromosuccinimide (0.078 mmol, 14 mg). The reaction mixture was allowed to stir at room temperature for 1 hour. After 1 hour, the reaction was concentrated in vacuo and the crude intermediate was dissolved in 1 mL TFA. The reaction mixture was stirred for 1 hour at room temperature and concentrated in vacuo to yield 6-bromo-3-(quinolin-3-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazolo[1,5-a]pyrimidin-7-amine as yellow solid.

Workup

  1. waitAfter 1 hour
  2. concentrationthe reaction was concentrated in vacuo
  3. dissolutionthe crude intermediate was dissolved in 1 mL TFA
  4. stirringThe reaction mixture was stirred for 1 hour at room temperature
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be7f832fef12479e993603631de4a1c6
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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