Hydrochloric Acid → HCID 23573427, compound

HRID 1824995Notes

Reaction equation

HRID 1824995 reaction equation
[NH:1]([C:8]([C:10]1[N:11]([CH2:27][C:28]([OH:30])=[O:29])[C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([NH:19][C:20](=[O:26])[CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:14][CH:13]=2)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:31](O)[CH3:32].CN(C)CCCN=C=NCC.Cl>CN(C)C1C=CN=CC=1.ClCCl>[NH:1]([C:8]([C:10]1[N:11]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([NH:19][C:20](=[O:26])[CH2:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[CH:14][CH:13]=2)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 23573394HCID 23573394, compound

Product 1

HCID 23573427HCID 23573427, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1.50 g (3.68 mmol) of {2-(anilinecarbonyl)-5-[(3,3-dimethylbutanoyl)amino]-1H-indol-1-yl}acetic acid from Example LIV, 225 mg (1.84 mmol) of 4-dimethylamino-pyridine and 203.5 mg (4.42 mmol) of ethanol are initially charged in dichloromethane. The mixture is cooled to 0° C., and 776 mg (4.05 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide×HCl are added. The mixture is stirred at RT for 4 hours. For work-up, the mixture is diluted and extracted with water and dichloromethane. The organic phase is dried with sodium sulphate, filtered and dried under reduced pressure. The resulting crude product is purified by column chromatography (silica gel 60, mobile phase: cyclohexane/ethyl acetate 2:1–1:1).

Workup

  1. additionFor work-up, the mixture is diluted
  2. extractionextracted with water and dichloromethane
  3. dry with materialThe organic phase is dried with sodium sulphate
  4. filtrationfiltered
  5. customdried under reduced pressure
  6. customThe resulting crude product is purified by column chromatography (silica gel 60, mobile phase: cyclohexane/ethyl acetate 2:1–1:1)

Sources & evidence

ORD record
ord-c0131a2249f1487381ec202cceb48c01
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

Loading…