N-(4-mercaptophenyl)cyclopropanecarboxamide → HCID 178518880, compound

HRID 1987604Notes

Reaction equation

HRID 1987604 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5]/[C:4](=[C:12]2/[C:13]([CH:18]3[CH2:20][CH2:19]3)=[N:14][NH:15][C:16]/2=[O:17])/[CH:3]=1.[SH:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([CH:31]2[CH2:33][CH2:32]2)=[O:30])=[CH:24][CH:23]=1>>[CH:18]1([C:13]2=[N:14][NH:15][C:16](=[O:17])/[C:12]/2=[C:4]2\[NH:5][C:6]3[C:11]([C:2]([S:21][C:22]4[CH:23]=[CH:24][C:25]([NH:28][C:29]([CH:31]5[CH2:32][CH2:33]5)=[O:30])=[CH:26][CH:27]=4)=[CH:3]\2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 16722082N-(4-mercaptophenyl)cyclopropanecarboxamideHCID 178518878HCID 178518878, compound

Product 1

HCID 178518880HCID 178518880, compound

Procedure

The title compound was prepared from (Z)-4-(4-chloroquinolin-2(1H)-ylidene)-3-cyclopropyl-1H-pyrazol-5(4H)-one and N-(4-mercaptophenyl)cyclopropanecarboxamide under conditions similar to those described in Example 6. The final compound was purified by precipitating it from methanol. 1H NMR (400 MHz, DMSO-D6) δ ppm 0.17-0.29 (m, 2H) 0.47-0.59 (m, 2H) 0.77-0.87 (m, 4H) 1.05-1.17 (m, 1H) 1.74-1.84 (m, 1H) 6.96 (s, 1H) 7.49-7.60 (m, 1H) 7.68 (d, J=8.59 Hz, 2H) 7.77-7.81 (m, 4H) 8.06 (d, J=7.07 Hz, 1H) 10.52 (s, 1H) 11.03 (s, 1H) 11.82 (s, 1H); ESI-MS: m/z calc'd for C25H22N4O2S 442.15. found 443.3 (M+H)+.

Workup

  1. customThe final compound was purified
  2. customby precipitating it from methanol

Sources & evidence

ORD record
ord-2a455da9b101481eb4609cbaa516ee38
Source dataset
uspto-grants-2009_06
Patent number
US07550598B2

Reaction notes

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