Ethyl Acetate → HCID 178521996, compound

HRID 407164Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:31])[NH:10][C:11]2[CH:12]=[C:13]([C:17]3[CH:25]=[C:24]4[C:20]([C:21]([C:26](OCC)=[O:27])=[N:22][NH:23]4)=[CH:19][CH:18]=3)[CH:14]=[CH:15][CH:16]=2)=[CH:4][C:3]=1[C:32]([F:35])([F:34])[F:33].[BH4-].[Li+].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[CH:25]=[C:24]4[C:20]([C:21]([CH2:26][OH:27])=[N:22][NH:23]4)=[CH:19][CH:18]=3)[CH:12]=2)=[O:31])=[CH:4][C:3]=1[C:32]([F:34])([F:33])[F:35]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of ethyl 6-(3-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenyl)-1H-indazole-3-carboxylate (73.7 mg) in tetrahydrofuran (5 Ml), was added lithium borohydride (0.44 Ml; LiBH4) at room temperature then, the mixture was stirred at 70° C. for 12 h. Saturated sodium bicarbonate solution and ethyl acetate were added. The aqueous layer was extracted with ethyl acetate and the combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography to give 1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(3-(3-(hydroxymethyl)-1H-indazol-6-yl)phenyl)urea (32.1 mg).

Workup

extractionThe aqueous layer was extracted with ethyl acetate
dry with materialthe combined organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by flash column chromatography

Sources & evidence

ORD record: ord-b03bbedaaf1343d999edd26bbbeb37a3
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754209B2

Reaction notes

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