Hydrochloric Acid → HCID 9960354, compound

HRID 1974568Notes

Reaction equation

HRID 1974568 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:9]1)=[O:7].C(N(C(C)C)CC)(C)C.[CH2:35]([C:39]1[CH:44]=[CH:43][C:42]([CH:45](Br)[C:46]2[CH:51]=[CH:50][C:49]([CH2:52][CH:53]([CH3:55])[CH3:54])=[CH:48][CH:47]=2)=[CH:41][CH:40]=1)[CH:36]([CH3:38])[CH3:37].Cl>ClCCl>[CH2:52]([C:49]1[CH:50]=[CH:51][C:46]([CH:45]([NH:2][C:3]2[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=2)[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:9]2)=[O:7])[C:42]2[CH:43]=[CH:44][C:39]([CH2:35][CH:36]([CH3:38])[CH3:37])=[CH:40][CH:41]=2)=[CH:47][CH:48]=1)[CH:53]([CH3:55])[CH3:54]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531Diisopropylethylamine2×HCID 19101766HCID 19101766, compound2×HCID 67785634HCID 67785634, compound

Product 1

HCID 9960354HCID 9960354, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[1-(3-aminobenzoyl)indol-3-yl]butyric acid hydrochloride (14.5 g) and diisopropylethylamine (22 ml) in dichloromethane (300 ml) was added bis(4-isobutylphenyl)methyl bromide (14.5 g) at room temperature. After stirring for 15 hours, diisopropylethylamine (7 ml) and bis(4-isobutylphenyl)methyl bromide 2.0 g) were added to the mixture. The mixture was stirred for 6 hours at room temperature and acidified by 7% hydrochloric acid (50 ml). The separated organic layer was washed with water and dried over magnesium sulfate. After the solvent was removed in vacuo, the residue was chromatographed on a column of silica gel (200 g) and eluted with chloroform to give a solid of 4-[1-[3-[bis(4-isobutylphenyl)methylamino]benzoyl]indol-3-yl]butyric acid (23.15 g).

Workup

  1. stirringThe mixture was stirred for 6 hours at room temperature
  2. washThe separated organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customAfter the solvent was removed in vacuo
  5. customthe residue was chromatographed on a column of silica gel (200 g)
  6. washeluted with chloroform

Sources & evidence

ORD record
ord-4c0e3c111fb2412eac59767598d5a528
Source dataset
uspto-grants-1994_02
Patent number
US05283251

Reaction notes

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