Methanimidamide, hydrochloride (1:1) → HCID 135407708, compound

HRID 871240Notes

Reaction equation

HRID 871240 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][O:15][CH3:16])[C:9]([O:17][CH3:18])=[CH:8][C:3]=1[C:4](OC)=[O:5].Cl.[CH:20](N)=[NH:21]>C(N)=O>[CH3:18][O:17][C:9]1[CH:8]=[C:3]2[C:2](=[CH:11][C:10]=1[O:12][CH2:13][CH2:14][O:15][CH3:16])[N:1]=[CH:20][NH:21][C:4]2=[O:5]

Participants

4

Reactant 2

HCID 10313058Methanimidamide, hydrochloride (1:1)HCID 66876535HCID 66876535, compound

Product 1

HCID 135407708HCID 135407708, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 713FormamideSolvent

Conditions

Temperature
140 °C

Procedure

According to the procedure described in Example 6A Step 4, a mixture of methyl 2-amino-5-methoxy-4-(2-methoxyethoxy)benzoate (2.69 g, 10.5 mmol) and formamidine hydrochloride (1.208 g, 15 mmol) in formamide (10 mL) was heated at 140° C. for 8 hours, to afford 6-methoxy-7-(2-methoxyethoxy)quinazolin-4(3H)-one as a white solid (1.935 g, 74%). 1H NMR (300 MHz, DMSO-d6) δ 12.1 (br, 1H), 7.98 (s, 1H), 7.44 (s, 1H), 7.14 (s, 1H), 4.23 (t, 2H), 3.87 (s, 3H), 3.72 (t, 2H), 3.32 (s, 3H); LC-MS (ESI) m/z 251 (M+H)+.

Sources & evidence

ORD record
ord-b444bfdb4b5c4e4ba0ae9cd47c2c28de
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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