Hydrochloric Acid → HCID 19787156, compound

HRID 1657176Notes

Reaction equation

HRID 1657176 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) δ 10.69 (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, 5H), 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-e48d8461732b43598e098575f71543b3
Source dataset
uspto-grants-1993_10
Patent number
US05256781

Reaction notes

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