Benzaldehyde → HCID 136027653, compound

HRID 1428882Notes

Reaction equation

HRID 1428882 reaction equation
C(=[O:8])C1C=CC=CC=1.[C:9]([C:11]1[CH:12]=[C:13]([CH:35]=[CH:36][CH:37]=1)[CH2:14][NH:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]=[C:21]([N:26]1[CH:30]=[C:29]([C:31]([OH:33])=[O:32])[CH:28]=[N:27]1)[NH:20][C:19]2=[O:34])#[N:10]>>[C:9]([C:11]1[CH:12]=[C:13]([CH:35]=[CH:36][CH:37]=1)[CH2:14][NH:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]=[C:21]([N:26]1[CH:30]=[C:29]([C:31]([OH:33])=[O:32])[CH:28]=[N:27]1)[NH:20][C:19]2=[O:34])(=[O:8])[NH2:10]

Participants

3

Reactant 2

HCID 240BenzaldehydeHCID 136027649HCID 136027649, compound

Product 1

HCID 136027653HCID 136027653, compound

Procedure

The titled compound was prepared in a manner analogous to Example 171, substituting 3-cyanobenzaldehyde for benzaldehyde in step A. Step C yielded a mixture of 1-[6-(3-cyano-benzylamino)-4-oxo-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid, the titled compound, and 1-[6-amino-4-oxo-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid, which was separated by reverse-phase HPLC.

Workup

  1. customStep C yielded
  2. customthe titled compound, and 1-[6-amino-4-oxo-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid, which was separated by reverse-phase HPLC

Sources & evidence

ORD record
ord-f93ac664e91c4548aae9f64cb022495c
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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