Dimethylformamide → HCID 68661530, compound

HRID 1022396Notes

Reaction equation

HRID 1022396 reaction equation
Cl[C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:18])[CH:8]=2)[N:3]=1.Cl.[CH2:20]([O:22][C:23](=[O:26])[CH2:24][NH2:25])[CH3:21].CN(C=O)C.C(N(CC)CC)C>O>[Cl:18][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:25][CH2:24][C:23]([O:22][CH2:20][CH3:21])=[O:26])[N:11]=[C:10]2[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 16282212,6-dichloro-4-phenylquinazolineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 68661530HCID 68661530, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To 550 mg of 2,6-dichloro-4-phenylquinazoline (compound No. Ia1-3) and 419 mg of glycine ethyl ester hydrochloride were added 3 ml of DMF and 607 mg of triethylamine, followed by stirring at 85° C. for 5.5 hours. The resulting reaction solution was poured into 100 ml of water and extracted with ethyl acetate. The extract was concentrated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1 to 3:1 to obtain 503 mg of the titled compound. Mp.146.1° C. 1H NMR (CDCl3): 1.30 (3H, t, J=7.2 Hz), 4.25 (2H, q, J=7.2 Hz), 4.31 (2H, d, J=5.2 Hz), 5.97 (1H, br. s), 7.54-7.63 (5H, m), 7.67-7.70 (2H, m), 7.79 (1H, s).

Workup

  1. customThe resulting reaction solution
  2. extractionextracted with ethyl acetate
  3. concentrationThe extract was concentrated
  4. customThe resulting residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-e9f2994e9ba747a7af6dded903bbb9e0
Source dataset
uspto-grants-2014_05
Patent number
US08722580B2

Reaction notes

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