5-Amino-8-quinolinecarboxamide → 5-((3S)-3-phenylazetidine-2-carboxamido)quinoline-8-carboxamide

HRID 2281020Notes

Reaction equation

HRID 2281020 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[CH2:25][C@H:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:23]1[C:32](O)=[O:33])=O)(C)(C)C>>[C:26]1([C@H:24]2[CH2:25][NH:22][CH:23]2[C:32]([NH:1][C:2]2[CH:11]=[CH:10][C:9]([C:12]([NH2:14])=[O:13])=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[N:7]3)=[O:33])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 896472255-Amino-8-quinolinecarboxamideHCID 89647751(3S)-1-(tert-butoxycarbonyl)-3-phenylazetidine-2-carboxylic acid

Product 1

HCID 896479805-((3S)-3-phenylazetidine-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 (3S)-1-(tert-butoxycarbonyl)-3-phenylazetidine-2-carboxylic acid, followed by de-Boc to afford Example 30. LC-MS (M+H=347, obsd=347).

Workup

  1. customdescribed for the preparation of Example 27
  2. customto afford Example 30

Sources & evidence

ORD record
ord-2e61de6e919d479b87b44fd2ca8ed3ae
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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