Hydrochloric Acid → HCID 10651442, compound

HRID 1974569Notes

Reaction equation

HRID 1974569 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[C:5]([N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[C:8]1[CH3:22])=[O:6].[CH2:26]([C:30]1[CH:35]=[CH:34][C:33]([CH:36](Cl)[C:37]2[CH:42]=[CH:41][C:40]([CH2:43][CH:44]([CH3:46])[CH3:45])=[CH:39][CH:38]=2)=[CH:32][CH:31]=1)[CH:27]([CH3:29])[CH3:28].C(N(C(C)C)CC)(C)C.Cl>ClCCl.C(OCC)(=O)C>[CH2:43]([C:40]1[CH:41]=[CH:42][C:37]([CH:36]([NH:1][C:2]2[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=2)[C:5]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[C:8]2[CH3:22])=[O:6])[C:33]2[CH:34]=[CH:35][C:30]([CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:31][CH:32]=2)=[CH:38][CH:39]=1)[CH:44]([CH3:46])[CH3:45]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 19010817Bis(4-isobutylphenyl)chloromethaneHCID 19101763HCID 19101763, compound

Product 1

HCID 10651442HCID 10651442, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 4-[1-(3-aminobenzoyl)-2-methylindol-3-yl]butyric acid (587 mg), bis(4-isobutylphenyl)methyl chloride (905 mg) and diisopropylethylamine (754 mg) in dichloromethane (20 ml) was stirred at 20° C. for 14 hours. The reaction mixture was poured into a mixture of ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. After evaporation of the solvent, the residue was chromatographed on a silica gel column (50 ml) eluting with a mixture of chloroform and methanol (50:1) to give 4-[1-[3-[bis(4-isobutylphenyl)methylamino]benzoyl]-2-methylindol-3-yl]butyric acid (720 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation of the solvent
  5. customthe residue was chromatographed on a silica gel column (50 ml)
  6. washeluting with a mixture of chloroform and methanol (50:1)

Sources & evidence

ORD record
ord-cb0415db6be14351abd6da6811c8c253
Source dataset
uspto-grants-1994_02
Patent number
US05283251

Reaction notes

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