(1S)-1-(4-Nitrophenyl)ethan-1-amine → (S)-Ethyl 2'-((2,3-dimethyl-5-((1-(4-nitrophenyl)ethyl)carbamoyl)-1H-indol-1-yl)methyl)-[1,1'-biphenyl]-4-carboxylate

HRID 1851947Notes

Reaction equation

HRID 1851947 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:18][N:19]2[C:27]3[C:22](=[CH:23][C:24]([C:28]([OH:30])=O)=[CH:25][CH:26]=3)[C:21]([CH3:31])=[C:20]2[CH3:32])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[N+:33]([C:36]1[CH:41]=[CH:40][C:39]([C@@H:42]([NH2:44])[CH3:43])=[CH:38][CH:37]=1)([O-:35])=[O:34]>>[CH3:32][C:20]1[N:19]([CH2:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:9]2[CH:8]=[CH:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:11][CH:10]=2)[C:27]2[C:22]([C:21]=1[CH3:31])=[CH:23][C:24]([C:28](=[O:30])[NH:44][C@H:42]([C:39]1[CH:38]=[CH:37][C:36]([N+:33]([O-:35])=[O:34])=[CH:41][CH:40]=1)[CH3:43])=[CH:25][CH:26]=2

Participants

3

Reactant 2

HCID 1268055(1S)-1-(4-Nitrophenyl)ethan-1-amineHCID 710743471-((4'-(Ethoxycarbonyl)-[1,1'-biphenyl]-2-yl)methyl)-2,3-dimethyl-1H-indole-5-carboxylic acid

Product 1

HCID 71099465(S)-Ethyl 2'-((2,3-dimethyl-5-((1-(4-nitrophenyl)ethyl)carbamoyl)-1H-indol-1-yl)methyl)-[1,1'-biphenyl]-4-carboxylate

Procedure

The title compound was prepared following the same protocol as described in Step 8, Example 1, using the 1-((4′-(ethoxycarbonyl)-[1,1′-biphenyl]-2-yl)methyl)-2,3-dimethyl-1H-indole-5-carboxylic acid instead of the 1-((2′-(tert-Butoxycarbonyl)biphenyl-4-yl)methyl)-2,3-dimethyl-1H-indole-5-carboxylic acid and the (S)-1-(4-nitrophenyl)ethanamine instead of the (S)-1-(4-bromophenyl)ethanamine.

Sources & evidence

ORD record
ord-666abe79c37d430680335b43c1251150
Source dataset
uspto-grants-2015_02
Patent number
US08957093B2

Reaction notes

Loading…