HCID 24715359, compound → HCID 59365117, compound

HRID 1645344Notes

Reaction equation

HRID 1645344 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[C:7]([O:12][CH2:13][CH3:14])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[C:15]([OH:17])=O)[CH3:2].[C:18]([O:22][C:23]([N:25]1[CH2:29][CH2:28][C@H:27]([O:30][C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=2)[CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>>[C:18]([O:22][C:23]([N:25]1[CH2:29][CH2:28][C@H:27]([O:30][C:31]2[CH:36]=[CH:35][C:34]([NH:37][C:15]([C:4]3[N:3]([CH2:1][CH3:2])[C:11]4[C:6]([CH:5]=3)=[C:7]([O:12][CH2:13][CH3:14])[CH:8]=[CH:9][CH:10]=4)=[O:17])=[CH:33][CH:32]=2)[CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

3

Reactant 2

HCID 24715359HCID 24715359, compoundHCID 25632275tert-Butyl (3S)-3-(4-aminophenoxy)pyrrolidine-1-carboxylate

Product 1

HCID 59365117HCID 59365117, compound

Procedure

The above nitro compound was hydrogenated under conditions as described in previous intermediate to provide (S)-3-(4-amino-phenyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester. The amide formation of N-ethyl-4-ethoxy-indole-2-carboxylic acid with (S)-3-(4-amino-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester under the same conditions as described in earlier intermediates preparation provided (S)-3-{4-[(4-ethoxy-1-ethyl-1H-indole-2-carbonyl)-amino]-phenoxy}-pyrrolidine-1-carboxylic acid tert-butyl ester. LCMS for C28H35N3O5 calcd. (m/e) 493, observed 494 (M+H).

Sources & evidence

ORD record
ord-5221da42a18146cca9bbc0c84e44005d
Source dataset
uspto-grants-2012_02
Patent number
US08124766B2

Reaction notes

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