Aniline → HCID 86754327, compound

HRID 583418Notes

Reaction equation

HRID 583418 reaction equation
[CH3:1][N:2]([CH:19]([CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]([CH3:35])[CH:27]=1)[CH2:20][CH2:21][C:22](O)=[O:23])[C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([C:14]([F:17])([F:16])[F:15])[CH:5]=1.[NH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[C:37]1([NH:36][C:22](=[O:23])[CH2:21][CH2:20][CH:19]([N:2]([CH3:1])[C:3](=[O:18])[C:4]2[CH:5]=[C:6]([C:14]([F:15])([F:16])[F:17])[CH:7]=[C:8]([C:10]([F:12])([F:11])[F:13])[CH:9]=2)[CH2:25][C:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]([CH3:35])[CH:27]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 21310527HCID 21310527, compound

Product 1

HCID 86754327HCID 86754327, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture consisting of 43.2 mg of 4-[N'-methyl-N'-(3,5-bis-trifluoromethyl-benzoyl)-amino]-5-(1-methyl-indol-3-yl)-pentanoic acid, 8.9 mg of aniline, 36.65 mg of propanephosphonic acid anhydride, 60 μl of triethylamine and 1.5 ml of methylene chloride is left to stand at room temperature for 16 hours. 0.5 ml of 1N potassium carbonate solution is then added and the mixture is shaken vigorously. After separation of the phases, the organic phase is separated off and concentrated by evaporation. In this way the title compound is obtained in the form of a white foam. Rf value=0.547 (ethyl acetate).

Workup

  1. waitis left
  2. customAfter separation of the phases
  3. customthe organic phase is separated off
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c14d82dbfb33461d8ba5293bfa8b13db
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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