Hydrochloric Acid → HCID 59416079, compound

HRID 2061812Notes

Reaction equation

[CH2:1]([NH:3][C:4](=[O:45])[NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]([C:22]2([CH2:28][OH:29])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:17]=[C:16]([C:30]([O:32]CC)=[O:31])[C:15]3=[O:35])=[C:8]([C:36]2[S:37][CH:38]=[C:39]([C:41]([F:44])([F:43])[F:42])[N:40]=2)[CH:7]=1)[CH3:2].C1COCC1.[Li+].[OH-].Cl>CO>[CH2:1]([NH:3][C:4](=[O:45])[NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]([C:22]2([CH2:28][OH:29])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:17]=[C:16]([C:30]([OH:32])=[O:31])[C:15]3=[O:35])=[C:8]([C:36]2[S:37][CH:38]=[C:39]([C:41]([F:44])([F:42])[F:43])[N:40]=2)[CH:7]=1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(4-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (Example 132, 0.225 g, 0.35 mmol) was diluted with 2:1 MeOH:THF (3 mL). A 2 M aq solution of LiOH (0.35 mL, 0.7 mmol) was added and the reaction mixture was heated in the microwave to 100° C. for 15 min. The mixture was conc in vacuo and acidified to approx. pH 3 with 1 N aq HCl. The resultant solid was collected and purified by column chromatography (silica 95:5 methylene chloride/methanol) followed by purification by reverse phase HPLC (C18, 0-95% acetonitrile/water gradient).

Workup

customThe resultant solid was collected
custompurified by column chromatography (silica 95:5 methylene chloride/methanol)
customfollowed by purification by reverse phase HPLC (C18, 0-95% acetonitrile/water gradient)

Sources & evidence

ORD record: ord-68610ee6058745b8bb0bf305a99e52b5
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283361B2

Reaction notes

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