1,1'-Carbonyldiimidazole → 3-phthalimidovaleric acid, 2-(7-chloro-5-phenyl-3H-1,4-benzodiazepin-2-yl)hydrazide

HRID 597091Notes

Reaction equation

HRID 597091 reaction equation
[C:1]1(=[O:18])[N:5]([CH:6]([CH2:11][CH3:12])[CH2:7][C:8]([OH:10])=O)[C:4](=[O:13])[C:3]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:2]12.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:31][C:32]1[CH:33]=[CH:34][C:35]2[N:41]=[C:40]([NH:42][NH2:43])[CH2:39][N:38]=[C:37]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:36]=2[CH:50]=1>O1CCCC1>[Cl:31][C:32]1[CH:33]=[CH:34][C:35]2[N:41]=[C:40]([NH:42][NH:43][C:8](=[O:10])[CH2:7][CH:6]([N:5]3[C:1](=[O:18])[C:2]4=[CH:17][CH:16]=[CH:15][CH:14]=[C:3]4[C:4]3=[O:13])[CH2:11][CH3:12])[CH2:39][N:38]=[C:37]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:36]=2[CH:50]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 123908747-Chloro-2-hydrazinyl-5-phenyl-3H-1,4-benzodiazepineHCID 214489983-Phthalimidovaleric acid

Product 1

HCID 867345683-phthalimidovaleric acid, 2-(7-chloro-5-phenyl-3H-1,4-benzodiazepin-2-yl)hydrazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In the manner given in Example 20, 3-phthalimidovaleric acid and carbonyldiimidazole are allowed to react in tetrahydrofuran. To this mixture is added 7-chloro-2-hydrazino-5-phenyl-3H-1,4-benzodiazepine to give 3-phthalimidovaleric acid, 2-(7-chloro-5-phenyl-3H-1,4-benzodiazepin-2-yl)hydrazide which is warmed with acetic acid to give N-[2-(8-chloro-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepin-1-yl)butyl]phthalimide

Sources & evidence

ORD record
ord-fc17c374ebc7414abb3ddfab9a8f8795
Source dataset
uspto-grants-1977_03
Patent number
US04012413

Reaction notes

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