Triethylamine → HCID 178483073, compound

HRID 1984937Notes

Reaction equation

HRID 1984937 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H:11]([CH2:14][NH2:15])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[C:18]1[N:27]=[C:26]([N:28]([CH3:30])[CH3:29])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1.C(N(CC)CC)C>CC(O)C>[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:9][CH2:10][C@@H:11]([CH2:14][NH:15][C:18]2[N:27]=[C:26]([N:28]([CH3:30])[CH3:29])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 126843422-Chloro-N,N-dimethylquinazolin-4-amineHCID 178453942HCID 178453942, compound

Product 1

HCID 178483073HCID 178483073, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of cis-(4-aminomethyl-cyclohexyl)-carbamic acid tert-butyl ester (1.14 g, 5 mmol), (2-chloro-quinazoline-4-yl)-dimethyl-amine obtained in step B of example 1 (1.035 g, 5 mmol), and triethylamine (1.5 mL, 11 mmol) in 2-propanol (2.5 mL) was heated at 170° C. for 35 min using a Smith Microwave Synthesizer. The mixture was concentrated and the residue was purified by column chromatography (silica gel, CH2Cl2 to 10% 2 M NH3/MeOH in CH2Cl2) to give cis-{4-[(4-dimethylamino-quinazolin-2-ylamino)-methyl]-cyclohexyl}-carbamic acid tert-butyl ester (1.28 g, 80%) as a white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by column chromatography (silica gel, CH2Cl2 to 10% 2 M NH3/MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-1393e29874734ad4afd5f6c8ee723104
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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