1-Hydroxybenzotriazole → {2-[5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}carbamic acid tert-butyl ester

HRID 1274386Notes

Reaction equation

HRID 1274386 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([CH3:25])([CH3:24])[C:21](O)=[O:22])[CH:18]=2)[NH:13][C:12]=1[C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[CH:27]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:35]1[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl.CCCCCCC>C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([CH3:24])([CH3:25])[C:21]([N:35]3[CH:39]4[CH2:40][CH2:41][CH:42]3[CH2:43][CH2:38]4)=[O:22])[CH:18]=2)[NH:13][C:12]=1[C:26]1[CH:27]=[C:28]([CH3:33])[CH:29]=[C:30]([CH3:32])[CH:31]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 154585232-[3-(2-tert-butoxycarbonylaminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acidHCID 20088687Heptane hydrochloride

Product 1

HCID 11114148{2-[5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}carbamic acid tert-butyl esterYield 86.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 2-[3-(2-tert-butoxycarbonylaminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid (247 mg in 3 mL dry methylene chloride) was added 1-hydroxybenzotriazole (111 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (126 mg) and the reagents allowed to mix for 1 hour. At this time a solution of 7-aza-bicyclo[2.2.]heptane hydrochloride (130 mg in 1.5 mL methylene chloride) was added followed by 0.15 mL triehtylamine and the reaction stirred at room temperature. After 20 hours, the mixture was concentrated in vacuo and purified by flash chromatography on silica gel (hexane:ethyl acetate, 1:1) to give the title compound (252 mg).

Workup

  1. additionto mix for 1 hour
  2. concentrationthe mixture was concentrated in vacuo
  3. custompurified by flash chromatography on silica gel (hexane:ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-7378895f928e4efea4c8b2f3461757e9
Source dataset
uspto-grants-2000_12
Patent number
US06156767

Reaction notes

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