4-(Dimethylamino)butanoyl chloride → HCID 178440384, compound

HRID 1987627Notes

Reaction equation

HRID 1987627 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.[CH3:28][N:29]([CH3:36])[CH2:30][CH2:31][CH2:32][C:33](Cl)=[O:34]>C1COCC1>[CH3:28][N:29]([CH3:36])[CH2:30][CH2:31][CH2:32][C:33]([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:34]

Participants

4

Reactant 2

HCID 150876904-(Dimethylamino)butanoyl chlorideHCID 178440359HCID 178440359, compound

Product 1

HCID 178440384HCID 178440384, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was synthesized using (Z)-4-(4-(4-aminophenylthio)quinolin-2(1H)-ylidene)-3-propyl-1H-pyrazol-5(4H)-one and 4-(dimethylamino)butanoyl chloride in THF according to the procedure described in the synthesis of Example 26. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.70 (t, J=7.33 Hz, 3H) 1.27-1.38 (m, J=7.45, 7.45, 7.45, 7.45 Hz, 2H) 1.90-1.99 (m, 2H) 2.21 (m, 2H) 2.44-2.49 (m, 2H) 2.81 (d, J=4.80 Hz, 6H) 3.07-3.15 (m, 2H) 6.76 (s, 1H) 7.57 (t, J=7.96 Hz, 1H) 7.69 (d, J=8.34 Hz, 2H) 7.79-7.90 (m, 4H) 8.09 (d, J=8.34 Hz, 1H) 9.43 (s, 1H) 10.40 (s, 1H); ESI-MS: m/z calc'd for C27H31N5O2S 489.63. found 490.3 (M+H)+.

Workup

  1. customdescribed in the synthesis of Example 26

Sources & evidence

ORD record
ord-25a31e7fb8834dca87e0482f5db1fd13
Source dataset
uspto-grants-2009_06
Patent number
US07550598B2

Reaction notes

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