N-bromobutanimide → HCID 58825057, compound

HRID 270953Notes

Reaction equation

HRID 270953 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:33]=[C:8]2[N:9]=[CH:10][C:11]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:21][CH:20]=3)=[C:12]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[N:7]2[N:6]=1)=[O:4].[Br:34]N1C(=O)CCC1=O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[C:33]([Br:34])=[C:8]2[N:9]=[CH:10][C:11]([C:19]3[CH:20]=[CH:21][C:22]([O:25][CH2:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[CH:23][CH:24]=3)=[C:12]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[N:7]2[N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 15957952HCID 15957952, compound

Product 1

HCID 58825057HCID 58825057, compoundYield 11.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice cold solution of 50 mg (0.113 mmol) of 6-(4-benzyloxy-phenyl)-7-cyclohexyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid methyl ester in 2 mL of dichloromethane (DCM) was added a solution of 21 mg (0.118 mmol) of N-bromosuccinimide (NBS) in 1 mL of DCM and the resulting mixture was allowed to warm up to rt and stirred at rt overnight. The reaction mixture was concentrated to give a residue which was chromatographed on silica gel (5% ethyl acetate in dichloromethane) to afford 7 mg (11% yield) of 6-(4-benzyloxy-phenyl)-3-bromo-7-cyclohexyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid methyl ester as a colorless oil as indicated by 1H NMR (90% purity); LC-MS—calcd for C27H26BrN3O3 [M++H]+: 520.12, found: 520.0.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give a residue which
  3. customwas chromatographed on silica gel (5% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-7d4bfd9cb1994d9597a3e6c59935f39f
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Reaction notes

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