Hydrochloric Acid → HCID 135556929, compound

HRID 2289294Notes

Reaction equation

HRID 2289294 reaction equation
[NH2:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[CH:14][CH:15]=[C:16]([NH:17][C:18]4[CH:39]=[CH:38][C:21]([C:22]([NH:24][C@H:25]([C:33]([O:35]CC)=[O:34])[CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])=[O:23])=[CH:20][CH:19]=4)[C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1.Cl>C(O)C.[OH-].[Na+]>[NH2:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[CH:14][CH:15]=[C:16]([NH:17][C:18]4[CH:19]=[CH:20][C:21]([C:22]([NH:24][C@H:25]([C:33]([OH:35])=[O:34])[CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[O:23])=[CH:38][CH:39]=4)[C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136046863HCID 136046863, compound

Product 1

HCID 135556929HCID 135556929, compoundYield 101.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of diethyl N-(4-((3-amino-1,2-dihydro-1-oxobenzo[f]-quinazolin-7-yl)amino)benzoyl)-L-glutamate (31 mg, 0.056 mmol) in ethanol (1 ml) and 0.25N NaOH (4 ml) was stirred under nitrogen at room temperature for 3 hours. The solution was then acidified to pH 3 with 1N hydrochloric acid and the resulting suspension allowed to stir for 15 minutes. The solid was filtered, washed with water, and dried under high vacuum to give N-(4-((3-amino-1,2-dihydro-1-oxobenzo[f]-quinazolin-7-yl)amino)benzoyl)-L-glutamic acid (27 mg). 1H NMR (DMSO-d6, 200 MHz) δ: 1.79-2.16 (m, 2H, glu CH2 ), 2.32 (t, J=7 Hz, 2H, glu CH2), 4.27-4.41 (m, 1H, glu CH), 6.55 (br s, 2H, NH2), 6.85 (d, J=9 Hz, 2H, Ar), 7.27 (d, J=9 Hz, 1H, Ar), 7.34 (d, J=7 Hz, 1H, Ar), 7.55 (t, J=8 Hz, 1H, Ar), 7.72 (d, J=9 Hz, 2H, Ar), 8.16 (d, J=9 Hz, 1H, Ar), 8.24 (d, J=8 Hz, 1H, glu NH), 8.62 (s, 1H, C7 --NH), 9.45 (d, J=9 Hz, 1H, Ar), 11.13 (br s, 1H, N2H), 12.31 (br s, 2H, CO2H's). Anal. Calculated for C24H21N5O6.5/4H2O: C, 57.89; H, 4.76; N, 14.06. Found: C, 57.93; H, 4.73; N 13.99.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with water
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-19b52a842244401f80aa96af531ad078
Source dataset
uspto-grants-2000_07
Patent number
US06090941

Reaction notes

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