Aniline → HCID 86754322, compound

HRID 583402Notes

Reaction equation

HRID 583402 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:15][C:16]([F:47])([F:46])[C:17]1[CH:18]=[C:19]([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:41]=1)[C:20]([N:22]([CH:24]([CH2:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[NH:32][CH:31]=1)[CH2:25][C:26](O)=[O:27])[CH3:23])=[O:21]>ClCCl>[C:2]1([NH:1][C:26](=[O:27])[CH2:25][CH:24]([N:22]([C:20](=[O:21])[C:19]2[CH:39]=[C:40]([C:42]([F:43])([F:44])[F:45])[CH:41]=[C:17]([C:16]([F:46])([F:15])[F:47])[CH:18]=2)[CH3:23])[CH2:29][C:30]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[NH:32][CH:31]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 53809354HCID 53809354, compound

Product 1

HCID 86754322HCID 86754322, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aniline (8.3 mg, 1.2 eq) is placed in dichloromethane (0.5 ml), and triethylamine (52 μl, 5 eq) and 3-[N'-(3,5-bistrifluoromethyl-benzoyl)-N'-methyl-amino]-4-(1H-indol-3-yl)-butanoic acid [Example 7(b)] (35 mg, 0.07 mmol) are added. Propanephosphonic acid anhydride (31.6 mg, 4 eq, in 0.5 ml of ethyl acetate/dichloromethane) is added and the mixture is left to stand at room temperature for 24 hours. The mixture is washed with 1N potassium carbonate solution (0.5 ml) and the solvent is concentrated by evaporation. The resulting title compound has an Rf value (ethyl acetate) of 0.69.

Workup

  1. waitthe mixture is left
  2. washThe mixture is washed with 1N potassium carbonate solution (0.5 ml)
  3. concentrationthe solvent is concentrated by evaporation

Sources & evidence

ORD record
ord-f1217f79b9844728b55dc746640d55fa
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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