1,1'-Carbonyldiimidazole → 3-phthalimidobutyric acid 2-[7-chloro-5-(o-fluorophenyl)-3H-1,4-benzodiazepin-2yl]hydrazide

HRID 597089Notes

Reaction equation

HRID 597089 reaction equation
[C:1]1(=[O:17])[N:5]([CH:6]([CH3:11])[CH2:7][C:8]([OH:10])=O)[C:4](=[O:12])[C:3]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:2]12.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:30][C:31]1[CH:32]=[CH:33][C:34]2[N:40]=[C:39]([NH:41][NH2:42])[CH2:38][N:37]=[C:36]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=3[F:49])[C:35]=2[CH:50]=1>O1CCCC1>[Cl:30][C:31]1[CH:32]=[CH:33][C:34]2[N:40]=[C:39]([NH:41][NH:42][C:8](=[O:10])[CH2:7][CH:6]([N:5]3[C:1](=[O:17])[C:2]4=[CH:16][CH:15]=[CH:14][CH:13]=[C:3]4[C:4]3=[O:12])[CH3:11])[CH2:38][N:37]=[C:36]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=3[F:49])[C:35]=2[CH:50]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 123908877-chloro-2-hydrazino-5-(o-fluorophenyl)-3H-1,4-benzodiazepineHCID 126123903-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)butanoic acid

Product 1

HCID 544086023-phthalimidobutyric acid 2-[7-chloro-5-(o-fluorophenyl)-3H-1,4-benzodiazepin-2yl]hydrazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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

Sources & evidence

ORD record
ord-d45c31ec60584e63ac2bee3614138e81
Source dataset
uspto-grants-1977_03
Patent number
US04012413

Reaction notes

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