Phenyl isocyanate → 4-{5-Phenyl-3-[3-(3-phenyl-ureido)-propyl]-pyrazol-1-yl}-benzenesulfonamide

HRID 508609Notes

Reaction equation

[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]1([C:16]2[N:20]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:23][CH:22]=3)[N:19]=[C:18](NC(NC3C=CC=C(C(F)(F)F)C=3)=O)[CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:10]1([C:16]2[N:20]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:23][CH:22]=3)[N:19]=[C:18]([CH2:3][CH2:2][CH2:1][NH:7][C:8]([NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:9])[CH:17]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Reactant 2

HCID 7672Phenyl isocyanate

HCID 52951272HCID 52951272, compound

Product 1

HCID 529518634-{5-Phenyl-3-[3-(3-phenyl-ureido)-propyl]-pyrazol-1-yl}-benzenesulfonamideYield 90%

Procedure

The titled compound was prepared in 90% yield from phenyl isocyanate using the procedure detailed for compound 7. mp 171.0-172.1° C. 1H NMR (300 MHz, DMSO-d6): δ 8.43 (s, 1H), 7.79 (d, J=9 Hz, 2H), 7.47-7.36 (m, 9H), 7.29-7.16 (m, 4H), 6.87 (t, J=7 Hz, 1H), 6.57 (s, 1H), 6.23 (t, J=6 Hz, 1H), 3.25-3.14 (m, 2H), 2.69 (t, J=8 Hz, 2H), 1.92-1.78 (m, 2H). MS (ESI) m/z: 476.18 (M+H+). Anal. Calcd for C25H25N5O3S.0.3CH4O: C, 62.63; H, 5.44; N, 14.43. Found: C, 62.63; H, 5.34; N, 14.41.

Sources & evidence

ORD record: ord-1d648592aba14892bbb0128f2e20102a
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096532B2

Reaction notes

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