HCID 1713529, compound → HCID 68781830, compound

HRID 2264402Notes

Reaction equation

HRID 2264402 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][C:6]([Cl:13])=[CH:7][CH:8]=2)[N:3]=1.[CH2:14]([O:16][C:17]1[CH:18]=[C:19]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]1)[CH3:15]>CC(N(C)C)=O>[Cl:13][C:6]1[CH:5]=[C:4]2[C:9]([C:10]([NH2:12])=[N:11][C:2]([NH:27][CH:24]3[CH2:25][CH2:26][N:21]([CH2:20][C:19]4[CH:28]=[CH:29][C:30]([O:31][CH3:32])=[C:17]([O:16][CH2:14][CH3:15])[CH:18]=4)[CH2:22][CH2:23]3)=[N:3]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 1713529HCID 1713529, compoundHCID 392574451-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine2×

Product 1

HCID 68781830HCID 68781830, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 2,7-dichloro-quinazolin-4-ylamine (32.1 mg, 0.15 mmol, 1.0 equiv; commercially available) and 1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine (47.6 mg, 0.18 mmol, 1.2 equiv; intermediate A1) in DMAc (2 mL) was heated by microwave irradiation to 200° C. for 15 min. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 22.0 mg (28%) of the title compound. MS (ISP): 442.4 [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-355dc9f623564fc78a28bf20314b8c00
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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