N-bromobutanimide → HCID 178482048, compound

HRID 2091609Notes

Reaction equation

HRID 2091609 reaction equation
[ClH:1].[NH2:2][C:3]1[N:4]=[CH:5][C:6]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([N:29]([CH:31]3[CH2:33][CH2:32]3)[CH3:30])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[N:7][C:8]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([OH:19])=[N:14][CH:13]=[CH:12]2.COC(OC)N(C)C.[Br:42]N1C(=O)CCC1=O>CN(C=O)C>[ClH:1].[NH2:2][C:3]1[N:4]=[CH:5][C:6]([C:20]2[CH:21]=[CH:22][C:23]([S:26]([N:29]([CH:31]3[CH2:32][CH2:33]3)[CH3:30])(=[O:27])=[O:28])=[CH:24][CH:25]=2)=[N:7][C:8]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([OH:19])=[N:14][CH:13]=[C:12]2[Br:42]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 78373Dimethylformamide dimethyl acetalHCID 178482050HCID 178482050, compound

Product 1

HCID 178482048HCID 178482048, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a room temperature slurry of 4-(5-amino-6-(1-hydroxyisoquinolin-6-yl)pyrazin-2-yl)-N-cyclopropyl-N-methylbenzenesulfonamide hydrochloride (1.00 g, 2.07 mmoL, prepared by general method C) in DMF (10 mL) was added 1,1-dimethoxy-N,N-dimethylmethanamine (1 mL). Within minutes, the slurry discharged to a solution. Then, N-bromosuccinimide (386 mg, 2.17 mmol) was added in one portion. After 1 h the reaction was concentrated and flashed over silica gel (4-8% MeOH/DCM eluent) to provide 4-(5-amino-6-(4-bromo-1-hydroxyisoquinolin-6-yl)pyrazin-2-yl)-N-cyclopropyl-N-methylbenzenesulfonamide hydrochloride (480 mg, 43% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.59-11.67 (br. s, 1H), 8.77 (s, 1H), 8.36 (d, J=8.3 Hz, 1H), 8.24-8.30 (m, 2H), 8.17 (d, J=1.5 Hz, 1H), 7.99 (dd, J=8.3, 1.5 Hz, 1H), 7.86 (d, J=8.5 Hz, 2H), 7.62 (d, J=6.0 Hz, 1H), 6.76 (br. s, 2H), 2.69 (s, 3H), 1.80-1.90 (m, 1H), 0.76 (s, 2H), 0.65-0.73 (m, 2H); MS (EI) m/z=527.4 [M+1]+.

Workup

  1. waitWithin minutes
  2. concentrationAfter 1 h the reaction was concentrated

Sources & evidence

ORD record
ord-7b70392d76e2463bb975896fc9b6e876
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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