1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl 2-(5-isopropyl-2,4-bis(4-methoxybenzyloxy)-N-(1-methyl-1H-indol-5-yl)benzamido)acetate

HRID 38065Notes

Reaction equation

HRID 38065 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[CH:20]([C:23]1[C:24]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][CH:45]=2)=[CH:25][C:26]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)=[C:27]([CH:31]=1)[C:28](O)=[O:29])([CH3:22])[CH3:21].C(N=C=NCCCN(C)C)C>ClCCl>[CH:20]([C:23]1[C:24]([O:42][CH2:43][C:44]2[CH:45]=[CH:46][C:47]([O:50][CH3:51])=[CH:48][CH:49]=2)=[CH:25][C:26]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)=[C:27]([CH:31]=1)[C:28]([N:11]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([CH3:1])[CH:3]=[CH:4]2)=[O:29])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 595889935-Isopropyl-2,4-bis(4-methoxybenzyloxy)benzoic acidHCID 59589001tert-butyl 2-(1-methyl-1H-indol-5-ylamino)acetate

Product 1

HCID 59589004tert-butyl 2-(5-isopropyl-2,4-bis(4-methoxybenzyloxy)-N-(1-methyl-1H-indol-5-yl)benzamido)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl 2-(1-methyl-1H-indol-5-ylamino)acetate (1) and 5-isopropyl-2,4-bis(4-methoxybenzyloxy)benzoic acid were dissolved in dichloromethane at room temperature. 1-Ethyl-3-(3-dimethylaminopropyl)-carbodiimide (EDC) was added to the reaction solution and stirred for 2 hours. Work-up with water and extracted with dichloromethane followed by drying and concentration produced tert-butyl 2-(5-isopropyl-2,4-bis(4-methoxybenzyloxy)-N-(1-methyl-1H-indol-5-yl)benzamido)acetate (2). Without further purification, compound 2 was treated with Lawesson's reagent in toluene at 100° C. produced tert-butyl 2-(5-isopropyl-2,4-bis(4-methoxybenzyloxy)-N-(1-methyl-1H-indol-5-yl)phenylthioamido)acetate (3) in 82% over 2 steps.

Workup

  1. extractionWork-up with water and extracted with dichloromethane
  2. customby drying
  3. concentrationconcentration

Sources & evidence

ORD record
ord-530b220a3efb48d787b5ae116070573c
Source dataset
uspto-grants-2013_09
Patent number
US08524712B2

Reaction notes

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