Ammonia → HCID 58256335, compound

HRID 1805227Notes

Reaction equation

HRID 1805227 reaction equation
[NH2:1][C@H:2](CO)CCC1C=CC([NH-])=CC=1.[NH2:14][C@H:15]([CH2:35][OH:36])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]([CH3:34])[C:25](=[O:33])[C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[CH:20][CH:19]=1.C([O-])(=O)C.[Na+].N#CBr.N>CO>[NH2:1][C:2]1[O:36][CH2:35][C@H:15]([CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([N:24]([CH3:34])[C:25](=[O:33])[C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)=[CH:22][CH:23]=2)[N:14]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 10476Cyanogen BromideHCID 517045Sodium AcetateHCID 86653291HCID 86653291, compound

Product 1

HCID 58256335HCID 58256335, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

N-[4-((S)-3-amino-4-hydroxy-butyl)-phenyl]-4-chloro-N-methyl-benzamide [4-((S)-3-amino-4-hydroxy-butyl)-phenyl]-amide (95 mg) was dissolved in methanol (3 ml) at room temperature before addition of sodium acetate (69.9 mg) and a solution of cyanogen bromide (39.1 mg) in methanol (1 ml) dropwise. The reaction mixture was stirred at room temperature for 36 hours, then aqueous ammonia 25% was added (214.5 μl) and stirring was continued for an another hour. The solvent was evaporated in vacuo and the residue purified by preparative HPLC to give N-{4-[2-((S)-2-amino-4,5-dihydro-oxazol-4-yl)-ethyl]-phenyl}-4-chloro-N-methyl-benzamide (10 mg) as a light yellow foam. Description. MS (ISP): 316.2 ([M+H]+).

Workup

  1. stirringstirring
  2. customThe solvent was evaporated in vacuo
  3. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-11be94620a964e2e8da992222a3ecc59
Source dataset
uspto-grants-2013_01
Patent number
US08354441B2

Reaction notes

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