Water → 4-[1-Amino-4-[2-(3-hydroxy-phenyl)-ethylamino]-1-(3-methyl-3H-imidazol-4-yl)-butyl]-2-fluoro-benzonitrile

HRID 413433Notes

Reaction equation

HRID 413433 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:30]S(C(C)(C)C)=O)([C:24]2[N:25]([CH3:29])[CH:26]=[N:27][CH:28]=2)[CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C)[CH:17]=2)=[CH:5][C:4]=1[F:37])#[N:2].B(Br)(Br)Br.O>C(Cl)Cl>[NH2:30][C:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([F:37])[CH:5]=1)([C:24]1[N:25]([CH3:29])[CH:26]=[N:27][CH:28]=1)[CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 865855192-Methyl-propane-2-sulfinic acid [1-(4-cyano-3-fluoro-phenyl)-4-[2-(3-methoxy-phenyl)-ethylamino]-1-(3-methyl-3-H-imidazol-4-yl)-butyl]-amide

Product 1

HCID 185332004-[1-Amino-4-[2-(3-hydroxy-phenyl)-ethylamino]-1-(3-methyl-3H-imidazol-4-yl)-butyl]-2-fluoro-benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Methyl-propane-2-sulfinic acid [1-(4-cyano-3-fluoro-phenyl)-4-[2-(3-methoxy-phenyl)-ethylamino]-1-(3-methyl-3-H-imidazol-4-yl)-butyl]-amide (0.075 g, 0.1427 mmol) was dissolved in CH2Cl2 (7 mL) with cooling in an ice-H2O bath, then treated with BBr3 (1 mL of a 1M solution in CH2Cl2, 1 mmol). After 15 min., H2O (3 mL) was added and the reaction mixture was concentrated in vacuo. The residue was dissolved in MeOH and stirred at ambient temperature for 15 min. Concentration to dryness gave the title compound which was used without further purification. MS (M+1) 408.

Workup

  1. temperaturewith cooling in an ice-H2O bath
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in MeOH
  4. concentrationConcentration to dryness

Sources & evidence

ORD record
ord-e2001d3c7d0c44c8893b3f00f01c88e6
Source dataset
uspto-grants-2003_05
Patent number
US06566385B2

Reaction notes

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