N-bromobutanimide → HCID 66896758, compound

HRID 1913211Notes

Reaction equation

HRID 1913211 reaction equation
[C:1]1([C:7]2C=C[N:10]=[CH:9][C:8]=2[C:13]2[CH:14]=[N:15][N:16]3[C:21]([N:22]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])=[CH:20][C:19]([CH:39]4[CH2:44][CH2:43][S:42](=[O:46])(=[O:45])[CH2:41][CH2:40]4)=[N:18][C:17]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N(Br)C(=O)C1>C(#N)C>[N:10]1[C:2]2[C:1](=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:7]=[C:8]([C:13]2[CH:14]=[N:15][N:16]3[C:21]([N:22]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:29])([CH3:30])[CH3:28])[CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:36])([CH3:37])[CH3:38])=[CH:20][C:19]([CH:39]4[CH2:40][CH2:41][S:42](=[O:46])(=[O:45])[CH2:43][CH2:44]4)=[N:18][C:17]=23)[CH:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66897754HCID 66897754, compound

Product 1

HCID 66896758HCID 66896758, compoundYield 110.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(4-phenyl-3-pyridyl)-5-(1,1-dioxo-tetrahydro-2H-thiopyran-4-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (Int-3a, 190 mg, 0.29 mmol) in acetonitrile (5 mL) was added NBS (51 mg, 0.29 eq). The mixture was stirred at rt for 2 h and concentrated. The residue was purified by Biotage (CH2Cl2/EtOAc, 20:1 to 4:1) to give 210 mg (99%) of the title compound as a light brown solid (Int-3b). LC/MS tR=2.55 (5 min method). Mass calculated for, M+H 757.20, observed 757.20 & 759.20 (doublet for Br).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by Biotage (CH2Cl2/EtOAc, 20:1 to 4:1)

Sources & evidence

ORD record
ord-f614c4498ef643c4a67e96455367db81
Source dataset
uspto-grants-2013_12
Patent number
US08609675B2

Reaction notes

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