Hydrochloric Acid → HCID 10817847, compound

HRID 1974571Notes

Reaction equation

HRID 1974571 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][C:12]([Cl:16])=[CH:13][CH:14]=2)[C:9]([CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:8]1)=[O:6].[CH2:26]([C:30]1[CH:35]=[CH:34][C:33]([CH:36](Br)[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>[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][C:12]([Cl:16])=[CH:13][CH:14]=3)[C:9]([CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:8]2)=[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531Diisopropylethylamine2×HCID 10618283HCID 10618283, compoundHCID 19101766HCID 19101766, compound2×

Product 1

HCID 10817847HCID 10817847, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 4-[1-(3-aminobenzoyl)-5-chloroindol-3-yl]butyric acid (700 mg), bis(4-isobutylphenyl)methyl bromide (705 mg) and diisopropylethylamine (620 mg) in dichloromethane (20 ml) was stirred at 20° C. for 1 hour, and then bis(4-isobutylphenyl)methyl bromide (150 mg) and diisopropylethylamine (70 mg) were added. After stirred at 20° C. for 3 hours, the reaction mixture was poured into iced 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 silica gel (20 g) eluting with a mixture of hexane and ethyl acetate (10:1 to 1:1) to give 4-[1-[3-[bis(4-isobutylphenyl)methylamino]benzoyl]-5-chloroindol-3-yl]butyric acid (803 mg).

Workup

  1. stirringAfter stirred at 20° C. for 3 hours
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was chromatographed on silica gel (20 g)
  7. washeluting with a mixture of hexane and ethyl acetate (10:1 to 1:1)

Sources & evidence

ORD record
ord-a4e6465312734b8f84b074a63a641ad1
Source dataset
uspto-grants-1994_02
Patent number
US05283251

Reaction notes

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