Sodium borohydride → Ammonia

HRID 269984Notes

Reaction equation

HRID 269984 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH:12]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:14][CH2:15][CH2:16][NH:17][S:18]([C:21]1[C:22]2[CH:23]=[CH:24][N:25]=[CH:26][C:27]=2[CH:28]=[C:29]([Br:31])[CH:30]=1)(=[O:20])=[O:19].[BH4-].[Na+]>C(Cl)Cl.CO>[NH3:1].[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][NH:14][CH2:15][CH2:16][NH:17][S:18]([C:21]2[C:22]3[CH:23]=[CH:24][N:25]=[CH:26][C:27]=3[CH:28]=[C:29]([Br:31])[CH:30]=2)(=[O:19])=[O:20])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 112982903-(4-Nitrophenyl)propanalHCID 58816122HCID 58816122, compound

Product 2

HCID 222AmmoniaHCID 866107517-Bromo-isoquinoline-5-sulfonic acid {2-[3-(4-nitro-phenyl)-propylamino]-ethyl}-amide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Add 3-(4-nitro-phenyl)-propionaldehyde (0.390 g, 2.18 mmol to 7-bromo-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide, [0.75 g (87% purity), 1.98 mmol) in 110 ml (6:5) CH2Cl2/MeOH. Stir the mixture for 18 h, then placed in an icebath. Add NaBH4 (0.150 g, 3.96 mmol) and stir for 1 h at 0° C. and 2 h at room temperature. Concentrate the reaction mixture, dissolve the residue in CH2Cl2/MeOH and load onto a silica gel column. Elute with 100% CH2Cl2, then a gradient of 0-10% (2M NH3 in MeOH) in CH2Cl2 to give 0.677 g of 7-bromo-isoquinoline-5-sulfonic acid {2-[3-(4-nitro-phenyl)-propylamino]-ethyl}-amide, as a yellow gum in 68% yield. ES Positive Ion MS [M+H]+ ions observed: m/z 493 (79 Br) and m/z 495 (81Br).

Workup

  1. concentrationConcentrate the reaction mixture
  2. dissolutiondissolve the residue in CH2Cl2/MeOH
  3. washElute with 100% CH2Cl2

Sources & evidence

ORD record
ord-ba96d066503d450ba5a69e3c3b199324
Source dataset
uspto-grants-2008_11
Patent number
US07449477B2

Reaction notes

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