Stannous Chloride → HCID 68553235, compound

HRID 2359901Notes

Reaction equation

HRID 2359901 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-])=O)=[C:7]([CH:11]=1)[C:8](O)=O.[CH3:15][O:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][NH2:20].C(C1NC=CN=1)([C:27]1[NH:28]C=CN=1)=O.[Sn](Cl)Cl>CN(C)C=O.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:11]=[C:7]2[C:6](=[CH:5][CH:4]=1)[N:12]=[C:27]([NH2:28])[N:20]([CH2:19][C:18]1[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=1[O:16][CH3:15])[CH2:8]2

Participants

7

Reactant 4

HCID 24479Stannous ChlorideHCID 812922-MethoxybenzylamineHCID 3392095-Methoxy-2-nitrobenzoic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 68553235HCID 68553235, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

6-Methoxy-3-(2-methoxybenzyl)-3,4-dihydroquinazolin-2-amine was synthesized from 5-methoxy-2-nitrobenzoic acid and 2-methoxybenzylamine by analogy with EXAMPLE 89. The peptide coupling was performed with carbonyl diimidazole and triethylamine in dimethylformamide. The nitro group was reduced with tin(II) chloride instead of iron(III) chloride to form the corresponding aniline. Subsequent cyclization to the dihydroquinazoline with cyanogen bromide was performed using a mixture of dichloromethane and ethanol.

Sources & evidence

ORD record
ord-a83b2f3ba5e44584b30b1d3fc037a08b
Source dataset
uspto-grants-2014_04
Patent number
US08686002B2

Reaction notes

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