2-chloro-6,7-dimethoxy-4-piperidin-1-ylquinazoline → HCID 68781515, compound

HRID 2264403Notes

Reaction equation

HRID 2264403 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([O:20][CH3:21])=[C:7]([O:18][CH3:19])[CH:8]=2)[N:3]=1.[CH2:22]([O:24][C:25]1[CH:26]=[C:27]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH2:28][N:29]1[CH2:34][CH2:33][CH:32]([NH2:35])[CH2:31][CH2:30]1)[CH3:23]>C(O)CO>[CH3:19][O:18][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][C:6]=1[O:20][CH3:21])[N:3]=[C:2]([NH:35][CH:32]1[CH2:33][CH2:34][N:29]([CH2:28][C:27]3[CH:36]=[CH:37][C:38]([O:39][CH3:40])=[C:25]([O:24][CH2:22][CH3:23])[CH:26]=3)[CH2:30][CH2:31]1)[N:11]=[C:10]2[N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 17135152-chloro-6,7-dimethoxy-4-piperidin-1-ylquinazolineHCID 392574451-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine2×

Product 1

HCID 68781515HCID 68781515, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A solution of 2-chloro-6,7-dimethoxy-4-piperidin-1-yl-quinazoline (30.8 mg, 0.10 mmol 1.0 equiv; commercially available) and 1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine (39.7 mg, 0.15 mmol, 1.5 equiv; intermediate A1) in ethylene glycol (2 mL) was heated by microwave irradiation to 220° C. for 20 min. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 8.7 mg (16%) of the title compound. MS (ISP): 391.4 [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-119a7e37ca0d4b0987771aa49bf63f18
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

Loading…