Water → HCID 18998817, compound

HRID 2260637Notes

Reaction equation

[OH:1][CH:2]([CH3:21])[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][C:15]([F:19])=[CH:16][CH:17]=3)[N:12]([CH3:20])[N:11]=2)[CH2:6][CH2:5]1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([N:34]=[C:35]=[O:36])[CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31].O.CCOCC>CN(C=O)C>[CH3:22][O:23][C:24]1[CH:25]=[C:26]([NH:34][C:35]([O:1][CH:2]([CH3:21])[CH2:3][N:4]2[CH2:5][CH2:6][CH:7]([C:10]3[C:18]4[C:13](=[CH:14][C:15]([F:19])=[CH:16][CH:17]=4)[N:12]([CH3:20])[N:11]=3)[CH2:8][CH2:9]2)=[O:36])[CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1-(2-hydroxyprop-1-yl)-4-(6-fluoro-1-methyl-1H -indazol-3-yl)piperidine (200 mg; 0.69 mmol) in 5 ml dry DMF was added 3,4,5-trimethoxyphenylisocyanate (200 mg; 0.96 mmol) in 3 ml dry DMF. The reaction mixture was heated to 100° C. for 2 h, followed by cooling to room temperature and addition of a mixture of 25 ml water and 150 ml ether. The reaction mixture was filtered and separated. The ether phase was washed with water, brine, dried with sodium sulphate and concentrated in vacuo. The crude product was purified by chromatography on silica gel 60 with ethyl acetate:methanol (9:1, v/v) as eluent. Concentration of the appropriate fractions gave 100 mg (29%) of the title compound. M.p. 74°-77° C.

Workup

temperatureby cooling to room temperature
filtrationThe reaction mixture was filtered
customseparated
washThe ether phase was washed with water, brine
dry with materialdried with sodium sulphate
concentrationconcentrated in vacuo
customThe crude product was purified by chromatography on silica gel 60 with ethyl acetate:methanol (9:1

Sources & evidence

ORD record: ord-fe708ededc5b4bf6b66a8c097805d823
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05478845

Reaction notes

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