1-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine → [1-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-[4-(2-fluoro-phenyl)-quinazolin-2-yl]-amine

HRID 2264401Notes

Reaction equation

HRID 2264401 reaction equation
Cl[C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:19]([O:21][C:22]1[CH:23]=[C:24]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[CH2:25][N:26]1[CH2:31][CH2:30][CH:29]([NH2:32])[CH2:28][CH2:27]1)[CH3:20]>CN1C(=O)CCC1>[CH2:19]([O:21][C:22]1[CH:23]=[C:24]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[CH2:25][N:26]1[CH2:27][CH2:28][CH:29]([NH:32][C:2]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH2:30][CH2:31]1)[CH3:20]

Participants

4

Reactant 2

HCID 392574451-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine2×HCID 860461424-(2-Fluorophenyl)-2-Chloro-quinazoline

Product 1

HCID 68782193[1-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-[4-(2-fluoro-phenyl)-quinazolin-2-yl]-amineYield 20.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 2-chloro-4-(2-fluoro-phenyl)-quinazoline (38.8 mg, 0.15 mmol, 1.0 equiv) and 1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine (47.6 mg, 0.18 mmol, 1.2 equiv; intermediate A1) in NMP (2 mL) was heated by microwave irradiation to 200° C. for 30 min. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 14.9 mg (20%) of the title compound. MS (ISP): 487.5 [M+H]+.

Workup

  1. customRemoval of the solvent
  2. customunder reduced pressure and purification by preparative HPLC on reversed phase
  3. washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-cd5698fd67ba4edb9d07e86cea97dcd9
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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