Hydrochloric Acid → 3-(7-bromo-1-oxoisoquinolin-2(1H)-yl)-N-cyclopropyl-4-methylbenzamide

HRID 506966Notes

Reaction equation

HRID 506966 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][C:7](=O)[N:8]([C:13]3[CH:14]=[C:15]([CH:22]=[CH:23][C:24]=3[CH3:25])[C:16]([NH:18][CH:19]3[CH2:21][CH2:20]3)=[O:17])[C:9]2=[O:12])=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO.C(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([C:13]3[CH:14]=[C:15]([CH:22]=[CH:23][C:24]=3[CH3:25])[C:16]([NH:18][CH:19]3[CH2:21][CH2:20]3)=[O:17])[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 67018556HCID 67018556, compound

Product 1

HCID 115964093-(7-bromo-1-oxoisoquinolin-2(1H)-yl)-N-cyclopropyl-4-methylbenzamideYield 14.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(7-bromo-1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)-N-cyclopropyl-4-methylbenzamide (1.13 g) in methanol (19 ml) and methylene chloride (45 ml) under an atmosphere of argon was added NaBH4 (114 mg) portionwise and the reaction stirred at room temperature for 17 hours. Concentrated hydrochloric acid (0.2 ml) was added and the reaction stirred for a further 1 hour. The reaction mixture was concentrated and the residue resuspended in methylene chloride, washed 2N HCl, dried (magnesium sulfate) and concentrated to give 3-(7-bromo-1-oxoisoquinolin-2(1H)-yl)-N-cyclopropyl-4-methylbenzamide as a brown solid (157 mg); NMR Spectrum: (DMSOd6) 0.55 (m, 2H), 0.70 (m, 2H), 2.10 (s, 3H), 2.85 (m, 1H), 6.80 (d, 1H), 7.42 (d, 1H), 7.51 (d, 1H), 7.78 (d, 1H), 7.79 (s, 1H), 7.89 (d, 1H), 7.97 (d, 1H), 8.35 (s, 1H), 8.44 (d, 1H); Mass Spectrum: M+H+ 421.

Workup

  1. stirringthe reaction stirred for a further 1 hour
  2. concentrationThe reaction mixture was concentrated
  3. washwashed 2N HCl
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5b5278d2c73a4ae9970d54ac111ad94d
Source dataset
uspto-grants-2010_08
Patent number
US07786115B2

Reaction notes

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