Tetrahydrofuran → HCID 178440388, compound

HRID 1987626Notes

Reaction equation

HRID 1987626 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12]/[C:11](=[C:19]3/[C:20]([CH2:25][CH2:26][CH3:27])=[N:21][NH:22][C:23]/3=[O:24])/[CH:10]=2)=[CH:4][CH:3]=1.CCC[C:31](Cl)=[S:32].[CH2:34]1C[O:37][CH2:36][CH2:35]1>>[CH3:31][S:32][CH2:34][CH2:35][C:36]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12]/[C:11](=[C:19]3/[C:20]([CH2:25][CH2:26][CH3:27])=[N:21][NH:22][C:23]/3=[O:24])/[CH:10]=2)=[CH:6][CH:7]=1)=[O:37]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 22343826Butanecarbothioyl chlorideHCID 178440359HCID 178440359, compound

Product 1

HCID 178440388HCID 178440388, compound

Procedure

The title compound was synthesized using (Z)-4-(4-(4-aminophenylthio)quinolin-2(1H)-ylidene)-3-propyl-1H-pyrazol-5(4H)-one and 3-methylthiopropionyl chloride in THF according to the procedure described in the synthesis of Example 26. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.69 (t, J=7.33 Hz, 3H) 1.26-1.36 (m, J=7.36, 7.36, 7.36, 7.36, 7.20 Hz, 2H) 2.11 (s, 3H) 2.17-2.27 (m, 2H) 2.68 (t, J=6.82 Hz, 2H) 2.78 (t, J=6.95 Hz, 2H) 6.75 (s, 1H) 7.61 (t, J=7.58 Hz, 1H) 7.66-7.72 (m, 2H) 7.82-7.92 (m, 4H) 8.12 (d, J=8.08 Hz, 1H) 10.36 (s, 1H); ESI-MS: m/z calc'd for C25H26N4O2S2 478.63. found 479.2 (M+H)+.

Workup

  1. customdescribed in the synthesis of Example 26

Sources & evidence

ORD record
ord-909ba347732547cb8ed5bc868dc7410a
Source dataset
uspto-grants-2009_06
Patent number
US07550598B2

Reaction notes

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