Tin dichloride dihydrate → 4-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-aminophenyl)piperidin-3-ol

HRID 1392415Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1([C:15]([NH:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=3[N+:31]([O-])=O)[CH2:20][CH:19]2[OH:34])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7].O.[Sn](Cl)Cl>C(O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1([C:15]([NH:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=3[NH2:31])[CH2:20][CH:19]2[OH:34])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7]

Participants

Conditions

Temperature: 80 °C

Procedure

To the solution of 4-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-nitrophenyl)piperidin-3-ol (7.0 g, 14.7 mmol) obtained in Step 1 in 70 ml of ethanol, was added tin (II) chloride hydrate (1.13 mg, 44.2 mmol). The reaction mixture was refluxed for about 4 hours at 80° C., and then cooled to room temperature and concentrated. The resulting residue was diluted with 100 ml of ethyl acetate, alkalized with 29% aqueous ammonia solution (pH 8), and then the resulting white solid was filtered out. 100 ml of distilled water was added to the resulting filtrate. The resulting organic layer was dried and concentrated on sodium sulfate to give the titled compound (5.1 g).

Workup

temperaturecooled to room temperature
concentrationconcentrated
additionThe resulting residue was diluted with 100 ml of ethyl acetate
filtrationthe resulting white solid was filtered out
addition100 ml of distilled water was added to the resulting filtrate
customThe resulting organic layer was dried
concentrationconcentrated on sodium sulfate

Sources & evidence

ORD record: ord-a4c00ecc03d1468c8ccd71128c4dd465
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07342027B2

Reaction notes

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