Ammonia → HCID 56967414, compound

HRID 1187763Notes

Reaction equation

HRID 1187763 reaction equation
[NH2:1][C@@H:2]([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:9][CH:8]=1)[CH2:3][OH:4].C([O-])(=O)C.[Na+].[N:26]#[C:27]Br.N>CO>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][C@H:2]3[CH2:3][O:4][C:27]([NH2:26])=[N:1]3)=[CH:8][CH:9]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 10476Cyanogen BromideHCID 517045Sodium AcetateHCID 67502477HCID 67502477, compound

Product 1

HCID 56967414HCID 56967414, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred suspension of (S)-2-amino-4-[4-(4-chloro-phenylamino)-phenyl]-butan-1-ol (210 mg) and sodium acetate (121 mg) in methanol (5 ml) was added dropwise a solution of cyanogen bromide (68 mg) in methanol (0.3 ml). The resulting pale yellow solution was then stirred at room temperature for 16 h. Aqueous ammonia solution (0.4 ml, 25%) was added dropwise and stirring was continued for a further hour. The mixture was then concentrated in vacuo and the residue was purified by column chromatography (Isolute® Flash-NH2 from Separtis; gradient: heptane/EtOAc/MeOH) to give (S)-4-{2-[4-(4-chloro-phenylamino)-phenyl]-ethyl}-4,5-dihydro-oxazol-2-ylamine (74 mg, 48%) as a yellow solid. MS (ISP): 318.1 ([{37Cl}M+H]+), 316.1 ([{35Cl}M+H]+).

Workup

  1. stirringstirring
  2. waitwas continued for a further hour
  3. concentrationThe mixture was then concentrated in vacuo
  4. customthe residue was purified by column chromatography (Isolute® Flash-NH2 from Separtis; gradient: heptane/EtOAc/MeOH)

Sources & evidence

ORD record
ord-880d0e5293ba43aeb4456cb865677c95
Source dataset
uspto-grants-2014_03
Patent number
US08673950B2

Reaction notes

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