Benzaldehyde → HCID 136027655, compound

HRID 1428883Notes

Reaction equation

HRID 1428883 reaction equation
C(=O)C1C=CC=CC=1.C(C1C=C(C=CC=1)C[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.C(C1C=C(C=CC=1)CNC1C=C2C(=CC=1)N=C(N1C=C(C(O)=O)C=N1)NC2=O)(=O)N>>[NH2:15][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]

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 136027649HCID 136027649, compoundHCID 136027653HCID 136027653, compound

Product 1

HCID 136027655HCID 136027655, 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, 1-[6-(3-carbamoyl-benzylamino)-4-oxo-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid, and the titled compound. The mixture was separated by reverse-phase HPLC; the titled compound was recovered as the trifluoroacetate salt.

Workup

  1. customThe titled compound was prepared in a manner analogous to Example 171
  2. customStep C yielded
  3. customThe mixture was separated by reverse-phase HPLC
  4. customthe titled compound was recovered as the trifluoroacetate salt

Sources & evidence

ORD record
ord-db5be0e064c54471ad39f779c438ad3f
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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