HCID 68710550, compound → HCID 24786070, compound

HRID 2239351Notes

Reaction equation

HRID 2239351 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]([O:15]C)=O)=[C:10](/[N:17]=[CH:18]/[N:19]([CH3:21])C)[CH:9]=2)=[CH:4][CH:3]=1.[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH:24]1[CH2:30][O:31][C:32]1[CH:33]=[C:34](CN)[CH:35]=[CH:36][CH:37]=1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]3[C:13](=[O:15])[N:19]([CH2:21][C:36]4[CH:35]=[CH:34][CH:33]=[C:32]([O:31][CH2:30][CH:24]5[CH2:25][N:26]([CH3:29])[CH2:27][CH2:28][N:23]5[CH3:22])[CH:37]=4)[CH:18]=[N:17][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 68710550HCID 68710550, compoundHCID 178499302HCID 178499302, compound

Product 1

HCID 24786070HCID 24786070, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was synthesized according to Example 13c from methyl 5-(4-chlorophenyl)-3-{[(1E)-(dimethylamino)methylene]amino}thiophene-2-carboxylate (0.427 g, 1.32 mmol) and 1-{3-[(1,4-dimethylpiperazin-2-yl)methoxy]phenyl}methanamine (0.300 g, 1.20 mmol) in MeOH (2 mL), the crude product was purified by flash chromatography using EtOAc:MeOH:TEA (100:10:1) to give the title compound. Yield: 0.315 g (48%). 1H NMR (400 MHz, CDCl3) δ 8.07 (s, 1H), 7.58-7.62 (m, 2H), 7.38-7.42 (m, 2H), 7.45 (s, 1H), 7.22-7.27 (m, 1H), 6.82-6.93 (m, 3H), 5.16 (s, 2H), 3.91-4.01 (m, 2H), 2.76-2.87 (m, 2H), 2.66-2.73 (m, 1H), 2.47-2.55 (m, 1H), 2.36-2.44 (m, 1H), 2.34 (s, 3H), 2.27 (s, 3H), 2.09-2.27 (m, 2H). MS (ESI+) 495.01 (M+1H+)

Workup

  1. customThe title compound was synthesized
  2. customthe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-5b60f6a42b0b44f29e47525e35c01640
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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