HCID 68708341, compound → HCID 131728134, compound

HRID 2239355Notes

Reaction equation

HRID 2239355 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:12]=[C:13]([CH2:17][NH2:18])[CH:14]=[CH:15][CH:16]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[S:30][C:29]([C:31]([O:33]C)=[O:32])=[C:28](/[N:35]=[CH:36]/N(C)C)[CH:27]=2)=[CH:22][CH:21]=1>CO>[C:31]([OH:33])(=[O:32])[CH3:29].[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[S:30][C:29]3[C:31](=[O:32])[N:18]([CH2:17][C:13]4[CH:14]=[CH:15][CH:16]=[C:11]([O:10][CH:7]5[CH2:8][CH2:9][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6]5)[CH:12]=4)[CH:36]=[N:35][C:28]=3[CH:27]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 68708341HCID 68708341, compoundHCID 178499302HCID 178499302, compound

Product 1

HCID 131728134HCID 131728134, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

1-{3-[(1-Isopropylpiperidin-4-yl)oxy]phenyl}methanamine (188 mg, 0.757 mmol) and methyl 5-(4-chlorophenyl)-3-{[(1E)-(dimethylamino)methylene]amino}thiophene-2-carboxylate (244 mg, 0.757 mmol) were dissolved in MeOH (2 ml). The reaction was heated in a microwave at 120° C. for 15 minutes, during which time a precipitate had been formed in the microwave vial. The precipitate was filtered off and washed with MeOH. The filtrate was purified by reversed phase HPLC yielding the title compound as a white solid. Yield: 37 mg (9%). 1H NMR (400 MHz, CDCl3) δ 8.08 (s, 1H), 7.59 (m, 2H), 7.43 (s, 1H), 7.39 (m, 2H), 7.24 (t, 1H, J=7.9 Hz), 6.91-6.87 (m, 2H), 6.81 (dd, 1H, J=7.9 Hz, J=2.1 Hz), 5.15 (s, 2H), 4.40 (m, 1H, J=2.8 Hz), 3.06 (m, 1H, J=6.5 Hz), 2.87 (m, 2H), 2.75-2.67 (m, 2H), 2.14 (m, 2H), 1.97 (s, 2H), 1.90 (m, 2H), 1.13 (d, 6H, J=6.6 Hz). 13C NMR (100 MHz, CDCl3) δ 177.0, 157.9, 157.7, 157.1, 151.6, 148.1, 137.5, 135.8, 131.7, 130.5, 129.9, 127.8, 123.3, 121.0, 120.7, 116.3, 115.5, 70.9, 55.3, 49.5, 44.4, 29.3, 23.3, 17.7. MS (ESI+) 494.0 (M+1H+).

Workup

  1. customhad been formed in the microwave vial
  2. filtrationThe precipitate was filtered off
  3. washwashed with MeOH
  4. customThe filtrate was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-a938dd2a2721425aa9397aa2dc4e490f
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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