Triethylamine → HCID 20583358, compound

HRID 411298Notes

Reaction equation

HRID 411298 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([N:15]([CH2:17][C:18]1([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[CH3:16])[N:7]=[C:6]2[NH2:30].Cl[C:32]([O:34][CH2:35][CH3:36])=[O:33].C(N(CC)CC)C>ClCCl.O>[CH2:35]([O:34][C:32]([N:21]1[CH2:20][CH2:19][C:18]([CH2:17][N:15]([C:8]2[N:7]=[C:6]([NH2:30])[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=2)[CH3:16])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:23][CH2:22]1)=[O:33])[CH3:36]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 11486612HCID 11486612, compound

Product 1

HCID 20583358HCID 20583358, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 6,7-dimethoxy-N2-(4-phenyl-piperidin-4-ylmethyl)-quinazoline-2,4-diamine 11 (375 mg), ethyl chloroformate, and triethylamine (250 μl) in dichloromethane (10 ml) was stirred at room temperature for 24 hours. The mixture was diluted with water and extracted with ethyl acetate. The product was chromatographed on silica gel to yield 4-{[(4-Amino-6,7-dimethoxy-quinazolin-2-yl)-methyl-amino]-methyl}-4-phenyl-piperidine-1-carboxylic acid ethyl ester 20, MS: 479 (M+).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe product was chromatographed on silica gel

Sources & evidence

ORD record
ord-e11c54c6028a424e96652506a5c72a0f
Source dataset
uspto-grants-2003_05
Patent number
US06559153B2

Reaction notes

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