2-Chloro-N,N-dimethylquinazolin-4-amine → HCID 178483081, compound

HRID 1984928Notes

Reaction equation

HRID 1984928 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]([CH3:14])[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl.[NH2:16][C@@H:17]1[CH2:22][CH2:21][C@H:20]([C:23]([NH2:25])=[O:24])[CH2:19][CH2:18]1>N1C=CC=CC=1>[CH3:13][N:12]([CH3:14])[C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([NH:16][C@@H:17]2[CH2:22][CH2:21][C@H:20]([C:23]([NH2:25])=[O:24])[CH2:19][CH2:18]2)[N:11]=1

Participants

4

Reactant 2

HCID 126843422-Chloro-N,N-dimethylquinazolin-4-amineHCID 178479556HCID 178479556, compound

Product 1

HCID 178483081HCID 178483081, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (2-chloro-quinazolin-4-yl)-dimethyl-amine obtained in step B of example 1 (31.05 g, 150 mmol) and cis-4-amino-cyclohexanecarboxylic acid amide hydrochloride (26.7 g, 150 mmol) in pyridine (150 mL) was stirred at reflux for overnight. The reaction mixture was concentrated and residue was dissolve in CH2Cl2. The organic layer was washed with saturated aqueous NaHCO3 and the aqueous layer was extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (silica gel, 2% to 10% 2 M NH3/MeOH in CH2Cl2) to give a slightly brown solid and the solid was recrystallized from CH2Cl2 to give cis-4-(4-dimethylamino-quinazolin-2-ylamino)-cyclohexanecarboxylic acid amide (20.6 g, 44%) as yellow crystals.

Workup

  1. temperatureat reflux for overnight
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionresidue was dissolve in CH2Cl2
  4. washThe organic layer was washed with saturated aqueous NaHCO3
  5. extractionthe aqueous layer was extracted with CH2Cl2
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (silica gel, 2% to 10% 2 M NH3/MeOH in CH2Cl2)
  10. customto give a slightly brown solid
  11. customthe solid was recrystallized from CH2Cl2

Sources & evidence

ORD record
ord-7fb7b88f4c8940d381029cfebb5cb281
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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