Ethanol → HCID 59415735, compound

HRID 2061815Notes

Reaction equation

[C:1]([O:5][C:6](=[O:48])[C@@H:7]([N:11]1[C:20]2[C:15](=[CH:16][C:17]([C:21]3[CH:22]=[N:23][C:24]([NH:36][C:37]([NH:39][CH2:40][CH3:41])=[O:38])=[CH:25][C:26]=3[C:27]3[S:28][CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[N:31]=3)=[CH:18][CH:19]=2)[C:14](=[O:42])[C:13]([C:43]([O:45]CC)=O)=[CH:12]1)[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH3:49][NH2:50].C(O)C>>[CH2:40]([NH:39][C:37](=[O:38])[NH:36][C:24]1[N:23]=[CH:22][C:21]([C:17]2[CH:16]=[C:15]3[C:20](=[CH:19][CH:18]=2)[N:11]([C@@H:7]([CH:8]([CH3:9])[CH3:10])[C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:48])[CH:12]=[C:13]([C:43](=[O:45])[NH:50][CH3:49])[C:14]3=[O:42])=[C:26]([C:27]2[S:28][CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[N:31]=2)[CH:25]=1)[CH3:41]

Participants

Reactant 3

HCID 702Ethanol

HCID 6329Methylamine

HCID 59415835HCID 59415835, compound

Product 1

HCID 59415735HCID 59415735, compound

Procedure

A solution of (S)-ethyl 1-(1-tert-butoxy-3-methyl-1-oxobutan-2-yl)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-4-oxo-1,4-dihydroquinoline -3-carboxylate (Example 137, 0.100 g, 0.15 mmol) in 33 wt. % methylamine solution in absolute ethanol (3 mL, 24.1 mmol) was heated in the microwave to 80° C. for 15 min. The mixture was conconcentrated in vacuo and purified by column chromatography (silica, 95:5 methylene chloride/methanol) to provide the desired product.

Workup

custompurified by column chromatography (silica, 95:5 methylene chloride/methanol)

Sources & evidence

ORD record: ord-be52fd85f6264cc0b1d6e2c594d7dcd3
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283361B2

Reaction notes

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