Hydrochloric Acid → tert-Butyl 4-({[5-[(3,3-dimethylbutanoyl)amino]-1-(2-fluorobenzyl)-1H-indol-2-yl]-carbonyl}amino)phenylcarbamate

HRID 1824987Notes

Reaction equation

HRID 1824987 reaction equation
[CH3:1][C:2]([CH3:28])([CH3:27])[CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[F:23])[C:11]([C:24]([OH:26])=O)=[CH:10]2)=[O:5].CN(C)CCCN=C=NCC.Cl.[NH2:41][C:42]1[CH:47]=[CH:46][C:45]([NH:48][C:49](=[O:55])[O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[CH:44][CH:43]=1>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH3:1][C:2]([CH3:27])([CH3:28])[CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[F:23])[C:11]([C:24]([NH:41][C:42]1[CH:43]=[CH:44][C:45]([NH:48][C:49](=[O:55])[O:50][C:51]([CH3:53])([CH3:52])[CH3:54])=[CH:46][CH:47]=1)=[O:26])=[CH:10]2)=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 688611tert-Butyl (4-aminophenyl)carbamateHCID 221446405-[(3,3-Dimethylbutanoyl)amino]-1-(2-fluorobenzyl)-1H-indole-2-carboxylic acid

Product 1

HCID 22144637tert-Butyl 4-({[5-[(3,3-dimethylbutanoyl)amino]-1-(2-fluorobenzyl)-1H-indol-2-yl]-carbonyl}amino)phenylcarbamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

50 mg (0.13 mmol) of 5-[(3,3-dimethylbutanoyl)amino]-1-(2-fluorobenzyl)-1H-indole-2-carboxylic acid from Example XXXIX, 37.6 mg (0.20 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide×HCl and 8 mg (0.07 mmol) of 4-dimethylaminopyridine are initially charged in DMF. 32.7 mg (0.16 mmol) of tert-butyl 4-aminophenylcarbamate are added, and the mixture is stirred at RT overnight. For work-up, the mixture is diluted and extracted with aqueous hydrochloric acid and dichloromethane. The organic phase is washed with sat. sodium chloride solution, dried with sodium sulphate, filtered and dried under reduced pressure.

Workup

  1. additionFor work-up, the mixture is diluted
  2. extractionextracted with aqueous hydrochloric acid and dichloromethane
  3. washThe organic phase is washed with sat. sodium chloride solution
  4. dry with materialdried with sodium sulphate
  5. filtrationfiltered
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-4186d6edcc4b44f086369ab3405273b7
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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