Triethylamine → HCID 86756510, compound

HRID 1531308Notes

Reaction equation

HRID 1531308 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=O.[ClH:8].[NH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([NH:19][C:20]([C:22]3[C:23]([C:29]4[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=4)=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=3)=[O:21])[CH:16]=2)[CH2:11]1.C(N(CC)CC)C.[BH4-]>CO>[ClH:8].[NH:3]1[CH:4]=[CH:5][N:1]=[C:2]1[CH2:6][NH:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([NH:19][C:20]([C:22]3[C:23]([C:29]4[CH:30]=[CH:31][C:32]([C:35]([F:36])([F:37])[F:38])=[CH:33][CH:34]=4)=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=3)=[O:21])[CH:16]=2)[CH2:11]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 249551H-imidazole-2-carbaldehydeHCID 28123BorohydrideHCID 86756511HCID 86756511, compound

Product 1

HCID 86756510HCID 86756510, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Imidazole-2-carboxaldehyde (2.45 g, 25.5 mmol) is added to a solution of 6-methyl-4′-trifluoromethyl-biphenyl-2-carboxylic acid (2-amino-indan-5-yl)-amide hydrochloride (11.1 g, 24.9 mmol) and triethylamine (5.05 mL, 50.0 mmol) in methanol (500 mL). The mixture is stirred at room temperature for 16 hours. Polymer supported borohydride (Aldrich, borohydride on Ambelite IR-400, 2.5 mmol/g, 10.0 g, 25.0 mmol) is added, the mixture stirred for 2 hours, filtered and concentrated under reduced pressure. The residue is taken up in ethanol (100 mL) and a saturated solution of hydrochloric acid gas in diethyl ether (10 mL) is added. The white precipitate is collected to yield 6-methyl-4′-trifluoromethylbiphenyl-2-carboxylic acid [2-(2-imidazolylmethylamino)-indan-5-yl] amide hydrochloride m.p. 240-242° C. Free base has m.p. 169-170° C.

Workup

  1. additionis added
  2. stirringthe mixture stirred for 2 hours
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additiona saturated solution of hydrochloric acid gas in diethyl ether (10 mL) is added
  6. customThe white precipitate is collected

Sources & evidence

ORD record
ord-55cd5dd2f8e1483c811d40ff99b19237
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

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