6-Aminoquinoline → HCID 131725571, compound

HRID 1745240Notes

Reaction equation

HRID 1745240 reaction equation
[CH2:1]([O:4][N:5]=[C:6]1[CH2:10][N:9]([C:11]([O:13]C(C)(C)C)=O)[C@H:8]([C:18]([OH:20])=O)[CH2:7]1)[CH:2]=[CH2:3].[O:21]=[C:22]1[C:27](C(Cl)=O)=[CH:26][CH:25]=[C:24]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[O:23]1.[N:36]1[C:45]2[C:40](=[CH:41][C:42]([NH2:46])=[CH:43][CH:44]=2)[CH:39]=[CH:38][CH:37]=1>>[CH2:1]([O:4][N:5]=[C:6]1[CH2:10][N:9]([C:11]([C:27]2[C:22](=[O:21])[O:23][C:24]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:25][CH:26]=2)=[O:13])[C@H:8]([C:18]([NH:46][C:42]2[CH:41]=[C:40]3[C:45](=[CH:44][CH:43]=2)[N:36]=[CH:37][CH:38]=[CH:39]3)=[O:20])[CH2:7]1)[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 113736-AminoquinolineHCID 222235122-oxo-6-pentyl-2H-pyran-3-carbonyl chlorideHCID 58714562(2S,4EZ)-4-[(allyloxy)imino)-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725571HCID 131725571, compound

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-4-[(allyloxy)imino]-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid, 2-oxo-6-pentyl-2H-pyran-3-carbonyl chloride, and 6-quinolinamine the title compound was obtained in 67% purity by LC/MS. MS(ESI+): m/z=503.2.

Sources & evidence

ORD record
ord-8654d5dc6fcd48c18ba56473231efd75
Source dataset
uspto-grants-2006_03
Patent number
US07018988B2

Reaction notes

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