HCID 178472230, compound → HCID 178432187, compound

HRID 869690Notes

Reaction equation

[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([CH3:26])[C:8]([C:12]3[CH:16]=[C:15]([NH:17][C:18](=[O:25])[CH2:19][C:20](OCC)=[O:21])[NH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1>CO.O1CCCC1.O.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([CH3:26])[C:8]([C:12]3[CH:16]=[C:15]4[N:17]=[C:18]([OH:25])[CH:19]=[C:20]([OH:21])[N:14]4[N:13]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a suspension of ethyl 3-{[3-(7-fluoro-3-methylquinoxalin-2-yl)-1H-pyrazol-5-yl]amino}-3-oxopropanoate (30.0 g, 84.0 mmol) in methanol (210 mL), tetrahydrofuran (210 mL) and water (210 mL) was added 4-dimethylaminopyridine (51.3 g, 420 mmol) at ambient temperature. After being stirred at 85° C. for 5 h, the reaction mixture was diluted with ethyl acetate (750 mL) and water (750 mL) at ambient temperature. And the insoluble material was filtered off. The filtrate was washed with water (450 mL). The combined aqueous layer was washed with ethyl acetate (500 mL×2), and acidified to pH 2 with conc. Hydrochloric acid (17.0 mL) at ambient temperature, and then stirred for overnight. The resulting precipitate was collected and washed with water to give 2-(7-fluoro-3-methylquinoxalin-2-yl)pyrazolo[1,5-a]pyrimidine-5,7-diol. MS (APCI): m/z 312 (M+H).

Workup

filtrationAnd the insoluble material was filtered off
washThe filtrate was washed with water (450 mL)
washThe combined aqueous layer was washed with ethyl acetate (500 mL×2)
customacidified to pH 2 with conc. Hydrochloric acid (17.0 mL) at ambient temperature
stirringstirred for overnight
customThe resulting precipitate was collected
washwashed with water

Sources & evidence

ORD record: ord-5488745a609649cab959ed48e91c38af
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969376B2

Reaction notes

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