Triethylamine → HCID 86592835, compound

HRID 2237595Notes

Reaction equation

HRID 2237595 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=1.C(N(CC)CC)C.[C:21]([O:25][C:26]([NH:28][C@@H:29]1[CH2:34][CH2:33][CH2:32][CH2:31][C@@H:30]1[NH2:35])=[O:27])([CH3:24])([CH3:23])[CH3:22]>C(Cl)Cl>[Cl:1][C:2]1[N:11]=[C:10]([NH:35][C@H:30]2[CH2:31][CH2:32][CH2:33][CH2:34][C@H:29]2[NH:28][C:26](=[O:27])[O:25][C:21]([CH3:23])([CH3:22])[CH3:24])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1514392(1R,2S)-N1-(tert-Butoxycarbonyl)-1,2-cyclohexanediamineHCID 142564832,4-Dichloro-6-methylquinazoline

Product 1

HCID 86592835HCID 86592835, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4.80 g of 2,4-dichloro-6-methylquinazoline in 100 ml of methylene chloride, 9.12 g of triethylamine and 5.31 g of (1S,2R)-2-(t-butoxycarbonylamino)cyclohexylamine were added, and then the mixture was stirred at room temperature for 24 hours. The reaction solution was concentrated, mixed with water, extracted with methylene chloride and then dried. The solvent was distilled off and the residue was purified by silica gel column chromatography (chloroform:methanol=20:1) to obtain 8.30 g of the desirable compound.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionmixed with water
  3. extractionextracted with methylene chloride
  4. customdried
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-dd1d60cd0b2c4923ac8fa23059014621
Source dataset
uspto-grants-2010_05
Patent number
US07718663B2

Reaction notes

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