Sodium Carbonate → 11-({[(1-Ethylpyrrolidin-2-yl)methyl]amino}acetyl)-5-methyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 2057379Notes

Reaction equation

HRID 2057379 reaction equation
Cl[CH2:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[N:8]([CH3:17])[C:7]2[CH:18]=[CH:19][CH:20]=[N:21][C:6]1=2)=[O:4].C(=O)([O-])[O-].[Na+].[Na+].[CH2:28]([N:30]1[CH2:34][CH2:33][CH2:32][C:31]1([CH3:36])N)[CH3:29].C1(N)C(F)=C(F)C(F)=C([NH2:46])C=1F.Cl.Cl>C(O)C>[CH2:28]([N:30]1[CH2:34][CH2:33][CH2:32][CH:31]1[CH2:36][NH:46][CH2:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[N:8]([CH3:17])[C:7]2[CH:18]=[CH:19][CH:20]=[N:21][C:6]1=2)=[O:4])[CH3:29]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 19933222HCID 19933222, compoundHCID 2032937011-(2-Chloroacetyl)-5,11-dihydro-5-methyl-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Product 1

HCID 305309911-({[(1-Ethylpyrrolidin-2-yl)methyl]amino}acetyl)-5-methyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

9.0 gm of 11-chloroacetyl-5,11-dihydro-5-methyl-6H-pyrido[2,3-b]-[1,4]benzodiazepin-6-one, 3.5 gm of sodium carbonate and 4 gm of 1-ethyl-2-amino-methyl-pyrrolidine were refluxed in 100 ml of ethanol for 1.5 hours. Then the hot mixture was suction-filtered, the filtrate was evaporated in vacuo to dryness, and the residue was recrystallized from acetonitrile and subsequently from ethyl acetate, yielding 48% of theory of the compound of the formula ##STR6## which had a melting point of 169°-171° C. Its dihydrochloride had a melting point of 196°-198° C. (from ethanol).

Workup

  1. filtrationThen the hot mixture was suction-filtered
  2. customthe filtrate was evaporated in vacuo to dryness
  3. customthe residue was recrystallized from acetonitrile and subsequently from ethyl acetate
  4. customyielding 48% of theory of the compound of the formula ##STR6## which

Sources & evidence

ORD record
ord-98b98a9f50a84cbd93c2a8d5aa8c0645
Source dataset
uspto-grants-1980_07
Patent number
US04210648

Reaction notes

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