Methanethiol → HCID 58551493, compound

HRID 2204282Notes

Reaction equation

HRID 2204282 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][C:13]3([C:27]4[CH:26]=[N:25][N:24]([CH3:28])[C:23]=4[C:22]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[O:16]3)[CH2:12][CH2:11]2)=[O:9])=[C:4]([O:29][CH3:30])[CH:3]=1.[CH3:31][SH:32]>CN(C=O)C>[CH3:30][O:29][C:4]1[CH:3]=[C:2]([S:32][CH3:31])[CH:7]=[CH:6][C:5]=1[C:8]([N:10]1[CH2:11][CH2:12][C:13]2([C:27]3[CH:26]=[N:25][N:24]([CH3:28])[C:23]=3[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:16]2)[CH2:14][CH2:15]1)=[O:9]

Participants

4

Reactant 2

HCID 878MethanethiolHCID 58551550HCID 58551550, compound

Product 1

HCID 58551493HCID 58551493, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (4-fluoro-2-methoxyphenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone (500 mg, 1.23 mmol) and methanethiol (172 mg, 2.45 mmol) in DMF (5 mL) was heated at 80° C. for 36 h. The reaction led to the desired product as well as O-demethylated version of the product. To the crude reaction mixture was added 3 eq of iodomethane to remethylate to the desired product. The reaction mixture was washed with 1N HCl, sat. aq. NaHCO3, and brine. The organics were dried over sodium sulfate and evaporated. The crude product was purified by column chromatography eluting with 50-100% ethyl acetate in hexanes to give (2-methoxy-4-(methylthio)phenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone (60%). ESI-MS m/z calc. 435.2, found 436.1 (M+1)+. Retention time: 1.53 minutes (3 min run).

Sources & evidence

ORD record
ord-4ab0195f56f749f7ac9cd8e09052e366
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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