HCID 62440092, compound → HCID 25112244, compound

HRID 1919547Notes

Reaction equation

HRID 1919547 reaction equation
[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][C:4]([N:7]=[C:8]=[N:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[O:19])=[CH:3][CH:2]=1.[CH3:28][NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1>>[C:1]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:6]=[CH:5][C:4]([N:7]2[CH:16]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:11]3[C:10](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:9]=[C:8]2[N:29]([CH3:28])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][N:35]2[CH2:36][CH2:37][CH2:38][CH2:39]2)=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 62440092HCID 62440092, compoundHCID 86641594HCID 86641594, compound

Product 1

HCID 25112244HCID 25112244, compound

Procedure

-nitrocinnamic acid (7) is reacted with methanol under acid catalyst to give methyl 2-nitrocinnamate (8), of which the nitro group is reduced preferably with SnCl22H2O to provide methyl 2-aminocinnamate (9). The compound (9) is reacted with triphenylphosphine, preferably in the presence of hexachloroethane and triethylamine to give methyl 3-[2-(triphenylphosphineimino)phenyl]acrylate (10). The compound (10) is reacted with 4-biphenylyl isocyanate in a suitable solvent to give methyl 3-[2-(4-biphenylyliminomethyleneamino)phenyl]acrylate (11). Then, the compound (11) is reacted with N-methyl-N-[5-(pyrrolidin-1-yl)pentyl]amine (6) obtained according to the above Reaction Scheme 1 in a suitable solvent to give 3-(4-biphenylyl)-2-[N-methyl-N-(5-pyrrolidin-1-ylpentyl)amino]-4-methoxycarbonylmethyl-3,4-dihydroquinazoline (12). This compound (12) is hydrolyzed preferably using LiOH/H2O to provide compound (13), which is reacted with benzylamine, preferably in the presence of 1-hydroxybenzotriazole (HOBT) and 1-[3-(dimethylamine)propyl]-3-ethylcarbodiimide hydrochloric acid (EDC) to give 4-(N-benzylacetamino)-3-(4-biphenylyl)-2- [N-(5-pyrrolidin-1-ylpentyl)-N-methylamino]-3,4-dihydroquinazoline (14).

Workup

  1. customobtained
  2. customaccording to the above Reaction Scheme 1 in a suitable solvent

Sources & evidence

ORD record
ord-e544ac53bc594946a0bab48e7ae8546a
Source dataset
uspto-grants-2012_05
Patent number
US08168646B2

Reaction notes

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