Hydrochloric Acid → N-{4-[(4-Methoxy-phenyl)-methyl-amino]-quinazolin-2-ylmethyl}-acetamide

HRID 1876189Notes

Reaction equation

HRID 1876189 reaction equation
Cl.Cl[CH2:3][C:4]1[N:13]=[C:12]([N:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.Cl[C:25]1[C:34]2C(=CC=CC=2)N=C(CCl)[N:26]=1.C[O:38]C1C=CC(NC)=CC=1.Cl>CC(O)C>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([N:14]([CH3:15])[C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([CH2:3][NH:26][C:25](=[O:38])[CH3:34])[N:13]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 22250N-Methyl-4-anisidineHCID 131575204-Chloro-2-(chloromethyl)quinazolineHCID 68515345HCID 68515345, compound

Product 1

HCID 59242014N-{4-[(4-Methoxy-phenyl)-methyl-amino]-quinazolin-2-ylmethyl}-acetamideYield 85%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(2-Chloromethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine hydrochloride: A suspension of 4-chloro-2-chloromethyl-quinazoline (7.383 g, 35.0 mmol) and (4-methoxy-phenyl)-methyl-amine (4.837 g, 35.3 mmol) in i-PrOH (50 mL) was treated with HCl (12 M, 1.5 mL, 18 mmol) and stirred at rt for 2 h. The resulting solid was collected by vacuum filtration, yielding 10.367 g (85%) of the title compound. 1H NMR (DMSO-d6) δ 7.80-7.94 (m, 2H), 7.40-7.80 (m, 2H), 7.26-7.34 (m, 1H), 7.07-7.15 (m, 2H), 6.83 (br d, 1H), 4.94 (s, 2H), 3.83 (s, 3H), 3.72 (s, 3H); LC-MS (ESI+; 314 ([M+H]+)).

Workup

  1. filtrationThe resulting solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-5a4b7532ef5f4255a686a7c6800d1c14
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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