Ammonia → HCID 58256406, compound

HRID 1805231Notes

Reaction equation

HRID 1805231 reaction equation
[NH2:1][C@H:2]([CH2:25][OH:26])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([C:15]2[C:16]3[CH:17]=[CH:18][N:19]=[CH:20][C:21]=3[CH:22]=[CH:23][CH:24]=2)(=[O:14])=[O:13])=[CH:7][CH:6]=1.C([O-])(=O)C.[Na+].[N:32]#[C:33]Br.N>CO>[NH2:32][C:33]1[O:26][CH2:25][C@H:2]([CH2:3][CH2:4][C:5]2[CH:10]=[CH:9][C:8]([NH:11][S:12]([C:15]3[C:16]4[CH:17]=[CH:18][N:19]=[CH:20][C:21]=4[CH:22]=[CH:23][CH:24]=3)(=[O:14])=[O:13])=[CH:7][CH:6]=2)[N:1]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 10476Cyanogen BromideHCID 517045Sodium AcetateHCID 67151542HCID 67151542, compound

Product 1

HCID 58256406HCID 58256406, compoundYield 6.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Isoquinoline-5-sulfonic acid [4-((S)-3-amino-4-hydroxy-butyl)-phenyl]-amide (109 mg) was dissolved in methanol (3 ml) at room temperature before addition of sodium acetate (72.2 mg) and a solution of cyanogen bromide (40.4 mg) in methanol (1 ml) dropwise. The reaction mixture was stirred at room temperature for 36 hours, then aqueous ammonia 25% was added (55 μl) and stirring was continued for an another hour. The solvent was evaporated in vacuo and the residue purified by Isco chromatography (column: Silicycle Si-Amine, AcOEt) to give isoquinoline-5-sulfonic acid {4-[2-((S)-2-amino-4,5-dihydro-oxazol-4-yl)-ethyl]-phenyl}-amide (7.8 mg) as a yellow solid. Description. MS (ISP): 397.2 ([M+H]+).

Workup

  1. stirringstirring
  2. customThe solvent was evaporated in vacuo
  3. customthe residue purified by Isco chromatography (column: Silicycle Si-Amine, AcOEt)

Sources & evidence

ORD record
ord-fc3612a97c024f3db31c4103959c0ce1
Source dataset
uspto-grants-2013_01
Patent number
US08354441B2

Reaction notes

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