Acetic Acid → HCID 22349638, compound

HRID 896270Notes

Reaction equation

HRID 896270 reaction equation
COC([C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:8]([O:21][CH3:22])=[CH:7][C:6]=1[C:23]#[N:24])=N.[NH2:25][C:26]1[S:27][CH:28]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:30]=1.[H-].[Na+].C(O)(=O)C.[CH3:43][N:44](C=O)C>>[CH3:22][O:21][C:8]1[CH:7]=[C:6]2[C:5](=[CH:10][C:9]=1[O:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1)[N:44]=[CH:43][N:25]([C:26]1[S:27][CH:28]=[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[N:30]=1)[C:23]2=[NH:24]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 403022-Amino-4-phenylthiazoleHCID 131725033HCID 131725033, compound

Product 1

HCID 22349638HCID 22349638, compound

Procedure

Methyl-2-cyano-4-methoxy-5-(3-morpholinopropoxy)phenylimidoformate (100 mg; 0.3 mmol) in DMF (1.5 ml) was reacted with 2-amino-4-phenyl-1,3-thiazole (58 mg; 0.33 mmol) in presence of sodium hydride (13.2 mg; 0.33 mmol) at 75° C. for 1.5 h. Acetic acid (1.5 eq.) was added and the solvent was evaporated to give 6-methoxy-7-(3-morpholinopropoxy)-3-(4-phenyl-1,3-thiazol-2-yl)quinazolin-4(3H)-imine as an intermediate which was redissolved in DMF (1.5 ml) and ammonium acetate (95 mg; 0.9 mmol) added. The mixture was stirred at 75° C. for 1 h, the solvent was evaporated and the residue purified by silica gel chromatography, CH2Cl2/MeOH 95/5→90/10 to give title compound (44 mg, 31%).

Workup

  1. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cf3a4158b53f4343b36ed6c5e64a98d4
Source dataset
uspto-grants-2005_07
Patent number
US06919338B2

Reaction notes

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