6-Aminoquinoline → HCID 131725535, compound

HRID 1349183Notes

Reaction equation

C(O[C:6]([N:8]1[CH2:12][C:11](=[N:13][O:14][CH3:15])[CH2:10][C@H:9]1[C:16]([OH:18])=O)=[O:7])(C)(C)C.[O:19]=[C:20]1[C:25](C(Cl)=O)=[CH:24][CH:23]=[C:22]([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[O:21]1.[N:34]1[C:43]2[C:38](=[CH:39][C:40]([NH2:44])=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1>>[CH3:15][O:14][N:13]=[C:11]1[CH2:12][N:8]([C:6]([C:25]2[C:20](=[O:19])[O:21][C:22]([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:23][CH:24]=2)=[O:7])[C@H:9]([C:16]([NH:44][C:40]2[CH:39]=[C:38]3[C:43](=[CH:42][CH:41]=2)[N:34]=[CH:35][CH:36]=[CH:37]3)=[O:18])[CH2:10]1

Participants

Reactant 3

HCID 113736-Aminoquinoline

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

HCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725535HCID 131725535, compound

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid, 2-oxo-6-pentyl-2H-pyran-3-carbonyl chloride, and 6-quinolinamine the title compound was obtained in 57% purity by LC/MS. MS(ESI+): m/z=477.2.

Sources & evidence

ORD record: ord-d59a2b23ee304fa8adafe7ad2fd3a6b6
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211601B2

Reaction notes

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