6-Aminoquinoline → HCID 131725501, compound

HRID 1349145Notes

Reaction equation

C(O[C:6]([N:8]1[CH2:12][C:11](=[N:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:10][C@H:9]1[C:24]([OH:26])=O)=[O:7])(C)(C)C.[O:27]=[C:28]1[C:33](C(Cl)=O)=[CH:32][CH:31]=[C:30]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[O:29]1.[N:42]1[C:51]2[C:46](=[CH:47][C:48]([NH2:52])=[CH:49][CH:50]=2)[CH:45]=[CH:44][CH:43]=1>>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][O:14][N:13]=[C:11]2[CH2:12][N:8]([C:6]([C:33]3[C:28](=[O:27])[O:29][C:30]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:31][CH:32]=3)=[O:7])[C@H:9]([C:24]([NH:52][C:48]3[CH:47]=[C:46]4[C:51](=[CH:50][CH:49]=3)[N:42]=[CH:43][CH:44]=[CH:45]4)=[O:26])[CH2:10]2)=[CH:21][CH:20]=1

Participants

Reactant 3

HCID 113736-Aminoquinoline

HCID 222235122-oxo-6-pentyl-2H-pyran-3-carbonyl chloride

HCID 58714542HCID 58714542, compound

Product 1

HCID 131725501HCID 131725501, compound

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-{[(4-methoxybenzyl)oxy]imino}-2-pyrrolidinecarboxylic acid, 2-oxo-6-pentyl-2H-pyran-3-carbonyl chloride, and 6-quinolinamine the title compound was obtained in 61% purity by LC/MS. MS(ESI+): m/z=583.4.

Sources & evidence

ORD record: ord-9ad949101f3e4d89825647961db2e5ce
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211601B2

Reaction notes

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