HCID 58551046, compound → HCID 58551711, compound

HRID 1908188Notes

Reaction equation

HRID 1908188 reaction equation
[CH:1]([S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([N:15]2[CH2:20][CH2:19][C:18]3([C:32]4[CH:31]=[N:30][N:29]([CH3:33])[C:28]=4[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:21]3)[CH2:17][CH2:16]2)=[O:14])=[C:9](OC)[CH:8]=1)(=[O:6])=[O:5])(C)C.F[C:37]1C=CC(C(N2CCC3(C4C=NN(C)C=4C4C=CC=CC=4O3)CC2)=O)=CC=1C.FC1C=CC(C(N2CCC3(C4C=NN(C)C=4C4C=CC=CC=4O3)CC2)=O)=C(C)C=1>>[CH3:33][N:29]1[C:28]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:21][C:18]3([CH2:19][CH2:20][N:15]([C:13]([C:10]4[CH:11]=[CH:12][C:7]([S:4]([CH3:1])(=[O:5])=[O:6])=[C:8]([CH3:37])[CH:9]=4)=[O:14])[CH2:16][CH2:17]3)[C:32]=2[CH:31]=[N:30]1

Participants

4

Reactant 3

HCID 58551046HCID 58551046, compoundHCID 58551161HCID 58551161, compoundHCID 67465365HCID 67465365, compound

Product 1

HCID 58551711HCID 58551711, compound

Procedure

A mixture of (2-methoxy-4-(methylthio)phenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone (320 mg, 0.74 mmol) and 30% hydrogen peroxide (250 μL) in acetic acid (3 mL) was heated at 80° C. for 45 min. The mixture was diluted with water and was extracted with ethyl acetate. The organics were washed with sat. aq. NaHCO3 and brine. The organics were dried over sodium sulfate and evaporated to dryness. The crude material was purified by column chromatography eluting with 70-100% ethyl acetate in hexanes to give (2-methoxy-4-(methylsulfonyl)phenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone. ESI-MS m/z calc. 467.2. found 468.2 (M+1)+. Retention time: 1.29 minutes (3 min run). 1H NMR (400 MHz, DMSO) δ 7.76-7.70 (m, 1H), 7.63-7.41 (m, 4H), 7.28 (t, J=7.7 Hz, 1H), 7.18-7.04 (m, 2H), 4.46-4.35 (m, 1H), 4.14-4.05 (m, 3H), 3.98-3.90 (m, 3H), 3.53-3.36 (m, 1H), 3.28 (s, 3H), 3.30-3.14 (m, 2H), 2.09-1.77 (m, 4H). (4-(Isopropylsulfonyl)-2-methoxyphenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone was also synthesized using the procedures described above. (1-Methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)(3-methyl-4-(methylsulfonyl)phenyl)methanone was synthesized from (4-fluoro-3-methylphenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone using the procedures described above. (4-(Isopropylsulfonyl)-2-methylphenyl)(1-methyl-1′-1-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone was synthesized from (4-fluoro-2-methylphenyl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone using the procedures above.

Workup

  1. customRetention time: 1.29 minutes (3 min run)

Sources & evidence

ORD record
ord-d058b78cfd0e4bdeac1f899e9c0041fa
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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