(4S)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid → 5-((4S)-4-phenylpyrrolidine-2-carboxamido)quinoline-8-carboxamide

HRID 2281018Notes

Reaction equation

HRID 2281018 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([NH2:14])=[O:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C(OC([N:22]1[CH2:26][C@H:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:24][CH:23]1[C:33](O)=[O:34])=O)(C)(C)C>>[C:27]1([C@H:25]2[CH2:26][NH:22][CH:23]([C:33]([NH:1][C:2]3[CH:11]=[CH:10][C:9]([C:12]([NH2:14])=[O:13])=[C:8]4[C:3]=3[CH:4]=[CH:5][CH:6]=[N:7]4)=[O:34])[CH2:24]2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 20828633(4S)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acidHCID 896472255-Amino-8-quinolinecarboxamide

Product 1

HCID 896471055-((4S)-4-phenylpyrrolidine-2-carboxamido)quinoline-8-carboxamide

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 27 by using 5-aminoquinoline-8-carboxamide coupled with (4S)-1-(tert-butoxycarbonyl)-4-phenylpyrrolidine-2-carboxylic acid, followed by removal of the protecting group to afford Example 28. LC-MS. (M+H=361, obsd=361).

Workup

  1. customdescribed for the preparation of Example 27
  2. customfollowed by removal of the protecting group
  3. customto afford Example 28

Sources & evidence

ORD record
ord-0607ed162809479b8c69e27c0c9eb8eb
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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