Acetic Acid → 2-Fluoro-4-(5-{[2-(3'-hydroxybiphenyl-2-yl)ethylamino]methyl}imidazol-1-ylmethyl)benzonitrile

HRID 278180Notes

Reaction equation

HRID 278180 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=1.[C:18]([C:20]1[CH:33]=[CH:32][C:23]([CH2:24][N:25]2[C:29]([CH:30]=O)=[CH:28][N:27]=[CH:26]2)=[CH:22][C:21]=1[F:34])#[N:19].[BH3-]C#N.[Na+].CC(O)=O>CO>[F:34][C:21]1[CH:22]=[C:23]([CH2:24][N:25]2[C:29]([CH2:30][NH:2][CH2:3][CH2:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=3)=[CH:28][N:27]=[CH:26]2)[CH:32]=[CH:33][C:20]=1[C:18]#[N:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 114247081-(4-Cyano-3-fluorobenzyl)-5-imidazolecarboxaldehydeHCID 226270951-Amino-2-(3'-hydroxybiphenyl-2-yl)ethane hydrochloride

Product 1

HCID 226270802-Fluoro-4-(5-{[2-(3'-hydroxybiphenyl-2-yl)ethylamino]methyl}imidazol-1-ylmethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-amino-2-(3′-hydroxybiphenyl-2-yl)ethane hydrochloride from Step C (0.47 mmol) and 1-(4-cyano-3-fluorobenzyl)-5-imidazolecarboxaldehyde from Example 3, Step G (112 mg, 0.49 mmol) were stirred in MeOH (1 mL) for 20 min, then NaCNBH3 (38 mg, 0.60 mmol) was added. The reaction mixture was adjusted to pH 5 with AcOH, as judged from wetted pH paper, and stirring was continued at ambient temperature for 18 hours. The reaction was quenched with 10% aq. citric acid and stirred for 20 min. Sat. aq. NaHCO3 (10 mL) was added and the mixture was extracted with CH2Cl2 (3×20 mL).

Workup

  1. customThe reaction was quenched with 10% aq. citric acid
  2. stirringstirred for 20 min
  3. additionSat. aq. NaHCO3 (10 mL) was added
  4. extractionthe mixture was extracted with CH2Cl2 (3×20 mL)

Sources & evidence

ORD record
ord-ad60dffc6be24b4ca587ff3f69033ec4
Source dataset
uspto-grants-2002_03
Patent number
US06358985B1

Reaction notes

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