Phenol → HCID 24785530, compound

HRID 2239325Notes

Reaction equation

HRID 2239325 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]([C:29]2[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=2)CN)[CH2:25][CH2:24]1.C1(O)C=CC=CC=1>CO>[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:35]4[CH:34]=[CH:31][CH:30]=[C:29]([N:26]5[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]5)[CH:36]=4)[CH:11]=[N:10][C:9]=3[CH:8]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 49612521-[3-(4-Methylpiperazin-1-yl)phenyl]methanamineHCID 11544322Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylate

Product 1

HCID 24785530HCID 24785530, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5-(4-chloro-phenyl)-3-(dimethylamino-methyleneamino)-thiophene-2-carboxylic acid methyl ester (0.189 g, 0.585 mmol), 3-(4-methyl-piperazin-1-yl)-benzylamine (0.100 g, 0.487 mmol) and phenol (1.0 g) was stirred at 130° C. for 1.5 hours. The reaction mixture was allowed to cool to r.t. and MeOH (10 mL) was added. After 30 minutes the precipitate was filtered off and washed with MeOH (50 mL). The crude product was purified by flash chromathography using a mixture of EtOAc, MeOH and TEA as eluent to give the product as an off white solid. Yield: 0.079 g (30%). 1H NMR (400 MHz, CDCl3) δ 8.08 (s, 1H), 7.60 (d, 2H, J=7.92 Hz), 7.44 (s, 1H), 7.40 (d, 2H, J=7.92 Hz), 7.22 (m, 1H), 6.92 (bs, 1H), 6.85 (d, 1H, J=7.92 Hz), 6.79 (d, 1H, J=7.46 Hz), 5.15 (s, 2H), 3.19 (m, 4H), 2.53 (m, 4H), 2.32 (s, 3H). MS (ESI+) 450.95 (M+1H+).

Workup

  1. temperatureto cool to r.t.
  2. filtrationAfter 30 minutes the precipitate was filtered off
  3. washwashed with MeOH (50 mL)
  4. customThe crude product was purified by flash chromathography
  5. additiona mixture of EtOAc, MeOH and TEA as eluent
  6. customto give the product as an off white solid

Sources & evidence

ORD record
ord-1b04a83a4d4b42a284222d1b9a47d57d
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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