Hydrochloric Acid → N-(4-(((3-amino-1,2-dihydro-1-oxobenzo[f]quinazolin-9-yl)-amino)sulfonyl)benzoyl)-L-glutamic acid

HRID 1884018Notes

Reaction equation

HRID 1884018 reaction equation
[NH2:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([NH:17][S:18]([C:21]4[CH:42]=[CH:41][C:24]([C:25]([NH:27][C@H:28]([C:36]([O:38]CC)=[O:37])[CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])=[O:26])=[CH:23][CH:22]=4)(=[O:20])=[O:19])[CH:15]=[CH:16][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1.Cl>[OH-].[Na+]>[NH2:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([NH:17][S:18]([C:21]4[CH:22]=[CH:23][C:24]([C:25]([NH:27][C@H:28]([C:36]([OH:38])=[O:37])[CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[O:26])=[CH:41][CH:42]=4)(=[O:20])=[O:19])[CH:15]=[CH:16][C:7]=3[CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136147908diethyl N-(4-(((3-amino-1,2-dihydro-1-oxobenzo[f]quinazolin-9-yl)amino)sulfonyl)benzoyl)-L-glutamate

Product 1

HCID 136076379N-(4-(((3-amino-1,2-dihydro-1-oxobenzo[f]quinazolin-9-yl)-amino)sulfonyl)benzoyl)-L-glutamic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of diethyl N-(4-(((3-amino-1,2-dihydro-1-oxobenzo[f]quinazolin-9-yl)amino)sulfonyl)benzoyl)-L-glutamate (0.175 g, 0.3 mmoles) in 1 N NaOH (12 ml) was stirred and heated to 50° C. under a nitrogen atmosphere for 24 hrs. After cooling,the solution was acidified (pH 3) with concentrated HCl to cause precipitation of the product which was filtered, washed with water and dried to give N-(4-(((3-amino-1,2-dihydro-1-oxobenzo[f]quinazolin-9-yl)-amino)sulfonyl)benzoyl)-L-glutamic acid as an off-white solid. (0.18 g, 99%) 1H NMR (DMSO-d6, 300 MHz) δ: 1.81-2.13 (m, 2H, glu-CH2); 2.32 (t, J=7.6 Hz, 2H, glu-CH2); 4.34 (m, 1H, glu-CH); 6.58 (br s, 2H, NH2); 7.16 (d, J=8.9 Hz, 1H, Ar); 7.22 (dd, J=8.6, 2 Hz, 1H, Ar); 7.74 (d, J=8.7 Hz, 1H, Ar); 7.89 (d, J=9.0 Hz, 1H, Ar); 7.96 (m, 4H, Ar); 8.78 (d, J=7.6 Hz, 1H, glu-NH); 9.49 (d, J=2 Hz, 1H, Ar); 10.68 (s, 1H, NH); 11.1 (br s, 1H, NH); 12.3 (br s, 2H, (CO2H)2). Anal. Calculated for C24H21N5O8S.3H2O: C, 48.56; H, 4.58; N, 11.80; S, 5.40. Found: C, 48.38; H, 4.30; N, 11.69; S. 5.34.

Workup

  1. customprecipitation of the product which
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-1c5b39da56a24ea4a3ed78338c0ab301
Source dataset
uspto-grants-2004_07
Patent number
US06762188B1

Reaction notes

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