Phenol → HCID 24785531, compound

HRID 2239326Notes

Reaction equation

HRID 2239326 reaction equation
CO[C:3]([C:5]1[S:6][C:7]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:8][C:9]=1[N:10]=[CH:11][N:12]([CH3:14])C)=[O:4].[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=2)CN)[CH2:25][CH2:24]1.C1(O)C=CC=CC=1>>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([C:7]2[S:6][C:5]3[C:3](=[O:4])[N:12]([CH2:14][C:32]4[CH:35]=[CH:36][CH:37]=[C:30]([CH2:29][N:26]5[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]5)[CH:31]=4)[CH:11]=[N:10][C:9]=3[CH:8]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 11544322Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylateHCID 167690511-{3-[(4-Methylpiperazin-1-yl)methyl]phenyl}methanamine

Product 1

HCID 24785531HCID 24785531, compound

Procedure

5-(4-Chloro-phenyl)-3-(dimethylamino-methyleneamino)-thiophene-2-carboxylic acid methyl ester (0.177 g, 0.547 mmol), 3-(4-methyl-piperazin-1-ylmethyl)-benzylamine (0.100 g, 0.456 mmol) and phenol (1.00 g) were stirred at 130° C. for 1.5 hours. The reaction mixture was allowed to cool to r.t. The product was partly purified by flash chromatography using EtOAc, MeOH and TEA mixtures as eluent to give a yellow solid. The solid was washed with MeOH to give the product. Yield: 0.122 g (48%). 1H NMR (400 MHz, CDCl3) δ 8.11 (s, 1H), 7.63 (d, 2H, J=8.52 Hz), 7.45 (s, 1H), 7.43 (d, 2H, J=8.52 Hz), 7.21-7.34 (m, 4H), 5.20 (s, 2H), 3.47 (s, 2H), 2.41 (bs, 8H), 2.25 (s, 3H). MS (ESI+) 464.93 (M+1H+).

Workup

  1. customThe product was partly purified by flash chromatography
  2. customto give a yellow solid
  3. washThe solid was washed with MeOH
  4. customto give the product

Sources & evidence

ORD record
ord-38af86ccbad540e09a89e23088e9dd30
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

Loading…