Triphosgene → benzyl-{2-[2-(3,5-dimethylphenyl)-5-isocyanato-1H-indol-3-yl]ethyl}-(4-Pyridin-3-yl-Butyl)amine

HRID 1532373Notes

Reaction equation

HRID 1532373 reaction equation
[CH2:1]([N:8]([CH2:29][CH2:30][CH2:31][CH2:32][C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1)[CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([NH2:20])[CH:18]=2)[NH:13][C:12]=1[C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[CH:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:40](Cl)([O:42]C(=O)OC(Cl)(Cl)Cl)Cl>N1C=CC=CC=1>[CH2:1]([N:8]([CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N:20]=[C:40]=[O:42])[CH:18]=2)[NH:13][C:12]=1[C:21]1[CH:22]=[C:23]([CH3:28])[CH:24]=[C:25]([CH3:27])[CH:26]=1)[CH2:29][CH2:30][CH2:31][CH2:32][C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 212498943-{2-[benzyl-(4-pyridin-3-yl-butyl)amino]ethyl}-2-(3,5-dimethylphenyl)-1H-indol-5-ylamine

Product 1

HCID 21249908benzyl-{2-[2-(3,5-dimethylphenyl)-5-isocyanato-1H-indol-3-yl]ethyl}-(4-Pyridin-3-yl-Butyl)amineYield 253.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-{2-[benzyl-(4-pyridin-3-yl-butyl)amino]ethyl}-2-(3,5-dimethylphenyl)-1H-indol-5-ylamine (120 mg in 8 mL dry methylene chloride) at 0° C. was added 26.6 mg triphosgene followed by 0.050 mL pyridine and the mixture stirred at low temperature. After 50 minutes, the mixture was concentrated in vacuo to give the crude title compound (120 mg).

Workup

  1. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-176ac33e69b744e0916739a4fe9a119c
Source dataset
uspto-grants-2001_03
Patent number
US06200957B1

Reaction notes

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