[3-(2-morpholinoethoxy)phenyl]methylamine → HCID 24785532, compound

HRID 2239327Notes

Reaction equation

HRID 2239327 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].[N:22]1([CH2:28][CH2:29][O:30][C:31]2[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=2)CN)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]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:33]4[CH:36]=[CH:37][CH:38]=[C:31]([O:30][CH2:29][CH2:28][N:22]5[CH2:23][CH2:24][O:25][CH2:26][CH2:27]5)[CH:32]=4)[CH:11]=[N:10][C:9]=3[CH:8]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7164624[3-(2-morpholinoethoxy)phenyl]methylamineHCID 11544322Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylate

Product 1

HCID 24785532HCID 24785532, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(4-Chlorophenyl)-3-(dimethylamino-methyleneamino)-thiophene-2-carboxylic acid methyl ester (0.164 g, 0.508 mmol), 3-(2-morpholin-4-yl-ethoxy)-benzylamine (0.100 g, 0.423 mmol) and MeOH (1.5 mL) were heated by MW at 120° C. for 15 minutes. The reaction mixture was allowed to cool to r.t., the precipitate filtered, washed with MeOH, and dried in vacuo to give the product. Yield: 0.110 g (45%). 1H NMR (400 MHz, CDCl3) δ 8.11 (s, 1H), 7.63 (d, 2H, J=8.42 Hz), 7.45 (s, 1H), 7.41 (d, 2H, J=8.42 Hz), 7.25 (m, 1H), 6.81-6.94 (m, 3H), 5.17 (s, 2H), 4.06 (t, 2H, J=6.12 Hz), 3.70 (t, 4H, J=4.68 Hz), 2.75 (t, 2H, J=5.58 Hz), 2.53 (t, 4H, J=4.51 Hz). MS (ESI+) 481.92 (M+1H+).

Workup

  1. filtrationthe precipitate filtered
  2. washwashed with MeOH
  3. customdried in vacuo
  4. customto give the product

Sources & evidence

ORD record
ord-10b371443b984ea7a063c718ca6412f0
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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