Triethylamine → HCID 136104957, compound

HRID 2244100Notes

Reaction equation

HRID 2244100 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[N:3]=1.CCN(CC)CC.[NH2:27][CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>C(Cl)Cl>[NH2:27][CH:28]1[CH2:33][CH2:32][N:31]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=3)[N:5]=[C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[OH:19])[N:3]=2)[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4243614-PiperidinamineHCID 1361050322-(4-Chloro-7-methylquinazolin-2-yl)-phenol

Product 1

HCID 136104957HCID 136104957, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 2-(4-Chloro-7-methylquinazolin-2-yl)-phenol (100 mg, 0.35 mmol), Et3N (72 μL, 0.52 mmol), and CH2Cl2 (300 μL) under N2, was added 4-aminopiperidine (54 μL, 0.52 mmol). The mixture was stirred at room temperature for 2 hours. The mixture was evaporated to dryness under reduced pressure. The residue was purified by silica gel chromatography using 98% CH2Cl2/2% MeOH to obtain the desired amine as a white solid (11 mg, 0.31 mmol, 89% yield). LC/MS (10-99%) M/Z 349.3 retention time 2.22 min.

Workup

  1. customThe mixture was evaporated to dryness under reduced pressure
  2. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-2fd98525034b4f20bb3aa83f31279566
Source dataset
uspto-grants-2010_03
Patent number
US07678802B2

Reaction notes

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