Methanimidamide, hydrochloride (1:1) → 6-(3-chloropropoxy)-7-methoxy-1H-quinazolin-4-one

HRID 871293Notes

Reaction equation

HRID 871293 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH2:15][CH2:16][CH2:17][Cl:18])=[CH:8][C:3]=1[C:4](OC)=[O:5].Cl.[CH:20](N)=[NH:21]>CCOC(C)=O>[Cl:18][CH2:17][CH2:16][CH2:15][O:14][C:9]1[CH:8]=[C:3]2[C:2](=[CH:11][C:10]=1[O:12][CH3:13])[N:1]=[CH:20][N:21]=[C:4]2[OH:5]

Participants

4

Reactant 2

HCID 10313058Methanimidamide, hydrochloride (1:1)HCID 23032997Methyl 2-amino-5-(3-chloropropoxy)-4-methoxybenzoate

Product 1

HCID 1784868706-(3-chloropropoxy)-7-methoxy-1H-quinazolin-4-oneYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2-amino-5-(3-chloropropoxy)-4-methoxybenzoate (6.0 g, 21.9 mmol) in EtOAc was reacted with formamidine hydrochloride in the manner described in Example 16A Step 4 to give 6-(3-chloropropoxy)-4-hydroxy-7-methoxyquinazoline (4.48 g, 16.7 mmol, 76%). 1H NMR (300 MHz, DMSO-d6) δ 12.10 (br s, 1H), 8.00 (s, 1H), 7.47 (s, 1H), 7.15 (s, 1H), 4.19 (t, 2H), 3.97 (s, 3H), 3.81 (t, 2H), 2.27-2.19 (m, 2H); LC-MS (ESI) m/z 269 (M+H)+.

Sources & evidence

ORD record
ord-5fd98f08b29e42539765305081b4b05b
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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