2-(Phenylhydrazono)-propanedioyl dichloride → 2-[2,4-Dioxo-3-(phenyl-hydrazono)-5-(1,3,5-trimethyl-1H-pyrazol-4-yl)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamide

HRID 1599084Notes

Reaction equation

[CH:1]([N:4]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[C:5](=[O:23])[CH2:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]1[C:16]([CH3:22])=[N:17][N:18]([CH3:21])[C:19]=1[CH3:20])([CH3:3])[CH3:2].[C:32]1([NH:38][N:39]=[C:40]([C:44](Cl)=[O:45])[C:41](Cl)=[O:42])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1>[O:45]=[C:44]1[N:7]([CH2:6][C:5]([N:4]([CH:1]([CH3:3])[CH3:2])[C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)=[O:23])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]([C:15]2[C:16]([CH3:22])=[N:17][N:18]([CH3:21])[C:19]=2[CH3:20])[C:41](=[O:42])[C:40]1=[N:39][NH:38][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of N-Isopropyl-N-(4-methoxy-phenyl)-2-[2-(1,3,5-trimethyl-1H-pyrazol-ylamino)-phenylamino]-acetamide (3.0 g, 7.1 mmol) in THF (70 mL) and a solution of 2-(phenyl-hydrazono)-propanedioyl dichloride (1.75 g, 7.1 mmol) in THF (70 mL) were simultaneously added to THF (35 mL) cooled to 0° C. The solution stirred at RT for 15 h and was subsequently concentrated in vacuo to yield the title compound (8.1 g) which was used without further purification.

Workup

concentrationwas subsequently concentrated in vacuo

Sources & evidence

ORD record: ord-e4dddf5b11614239ba7f86f518397bcc
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739129

Reaction notes

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