Acetyl chloride → (2-Acetamido-quinazolin-4-yl)-(4-methoxy-phenyl)-methylamine

HRID 1668805Notes

Reaction equation

HRID 1668805 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[C:29](Cl)(=[O:31])[CH3:30]>CN(C1C=CN=CC=1)C.ClCCl>[C:29]([NH:1][C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)(=[O:31])[CH3:30]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 11323466(2-Amino-quinazolin-4-yl)-(4-methoxy-phenyl)-methylamine

Product 1

HCID 11551535(2-Acetamido-quinazolin-4-yl)-(4-methoxy-phenyl)-methylamine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from (2-amino-quinazolin-4-yl)-(4-methoxy-phenyl)-methylamine (20 mg, 0.07 mmol), triethylamine (0.02 ml, 0.14 mmol), acetyl chloride (0.01 ml, 0.14 mmol) and DMAP (1 mg) in 2 ml of dichloromethane similar to example 28 to give 3 mg (13.6%) of white solids. 1H NMR (CDCl3): 7.88 (s, 1H), 7.62 (d, J=8.1 Hz, 1H), 7.52-7.47 (m, 1H), 7.15-7.12 (m, 2H), 6.95-6.86 (m, 4H), 3.85 (s, 3H), 3.55 (s, 3H), 2.68 (s, 3H).

Sources & evidence

ORD record
ord-d663ca8b7eef42b28c22f42b96aa6d30
Source dataset
uspto-grants-2011_08
Patent number
US07989462B2

Reaction notes

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