6-Chloro-1H-indole-2-carboxylic acid → (R)-3-{[(6-chloro-1H-indole-2-carbonyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1162679Notes

Reaction equation

HRID 1162679 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.[Cl:15][C:16]1[CH:24]=[C:23]2[C:19]([CH:20]=[C:21]([C:25](O)=[O:26])[NH:22]2)=[CH:18][CH:17]=1>>[C:11]([O:10][C:8]([N:5]1[CH2:6][CH2:7][C@H:3]([CH2:2][NH:1][C:25]([C:21]2[NH:22][C:23]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[C:16]([Cl:15])[CH:24]=3)=[O:26])[CH2:4]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 855846-Chloro-1H-indole-2-carboxylic acidHCID 1515152tert-Butyl (3R)-3-(aminomethyl)pyrrolidine-1-carboxylate

Product 1

HCID 58748222(R)-3-{[(6-chloro-1H-indole-2-carbonyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Procedure

68.1 Using general procedure E, (R)-3-aminomethyl-1-N-tert-butoxycarbonyl-pyrrolidine was coupled with 6-chloro-1H-indole-2-carboxylic acid to give (R)-3-{[(6-chloro-1H-indole-2-carbonyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester. Pale yellow solid. MS376.1 ([M−H]−)

Sources & evidence

ORD record
ord-c4083fe3591140bb99de0cde28ef81b0
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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