Hydrochloric Acid → HCID 19787156, compound

HRID 2082020Notes

Reaction equation

HRID 2082020 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][NH:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[NH:22][C:21](=[O:29])[N:20]=3)=[CH:13][CH:12]=2)=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:4].[OH-].[Na+].Cl>CO>[O:29]=[C:21]1[N:20]=[C:19]([NH:18][CH2:17][C:14]2[CH:15]=[CH:16][C:11]([C:6]3[C:5]([C:3]([OH:4])=[O:2])=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:12][CH:13]=2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53838656HCID 53838656, compound

Product 1

HCID 19787156HCID 19787156, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.26 g of 4'-[[(1,2-dihydro-2-oxo-4-quinazolinyl)amino]methyl][1,1'-biphenyl]-2-carboxylic acid methyl ester in 5.0 mL of methanol was added 15 mL of 0.1N aqueous sodium hydroxide. The solution was warmed to ~90° C. for 3 days. After cooling to room temperature the solution was neutralized with 0.1N HCl and the resulting precipitate was filtered off and washed with water. After drying, the solid was purified on silica gel chromatography to yield 0.160 g (64%) of the desired product. The product was characterized as its sodium salt: 1H NMR (DMSO-d6, 400 MHz) δ10.69 (s, 1H), 9.00 (t, J=5.8 Hz, 1H), 8.11 (d, J=8.0 Hz, 1H), 7.52 (m, 1H), 7.41 (d, J=8.2 Hz, 2H), 7.28 (m, 3H), 7.14 (m, 5 H), 4.68 (d, J=5.6 Hz, 2H); negative FAB MS m/e 392 (M--H); 370 (M--Na). Anal. Calcd for C22H16N3NaO3.1H2O: C, 64.23; H, 4.41; N, 10.21. Found: C, 64.43; H, 4.19; N, 9.82.

Workup

  1. temperatureThe solution was warmed to ~90° C. for 3 days
  2. filtrationthe resulting precipitate was filtered off
  3. washwashed with water
  4. customAfter drying
  5. customthe solid was purified on silica gel chromatography

Sources & evidence

ORD record
ord-991f865b91c54453b79d7448e5233bbc
Source dataset
uspto-grants-1993_02
Patent number
US05187168

Reaction notes

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