Sodium Hydroxide → tert-butyl N-[2-[[3-[[(Z)-(5-nitro-2-oxo-1H-indol-3-ylidene)-phenylmethyl]amino]phenyl]methylamino]-2-oxoethyl]carbamate

HRID 24849Notes

Reaction equation

HRID 24849 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=2)[C:6](=[C:16](OCC)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5]1=[O:26])(=O)C.[C:27]([O:31][C:32]([NH:34][CH2:35][C:36]([NH:38][CH2:39][C:40]1[CH:41]=[C:42]([CH:44]=[CH:45][CH:46]=1)[NH2:43])=[O:37])=[O:33])([CH3:30])([CH3:29])[CH3:28].[OH-].[Na+]>CN(C=O)C.CO>[C:27]([O:31][C:32]([NH:34][CH2:35][C:36]([NH:38][CH2:39][C:40]1[CH:41]=[C:42]([NH:43]/[C:16](=[C:6]2\[C:5](=[O:26])[NH:4][C:12]3[C:7]\2=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=3)/[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:44]=[CH:45][CH:46]=1)=[O:37])=[O:33])([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 542801041-Acetyl-3-{1-ethoxy-1-phenylmethylidene}-5-nitro-2-indolinoneHCID 697403253-Tert.butoxycarbonylaminomethylcarbonylaminomethyl-aniline

Product 1

HCID 178453820tert-butyl N-[2-[[3-[[(Z)-(5-nitro-2-oxo-1H-indol-3-ylidene)-phenylmethyl]amino]phenyl]methylamino]-2-oxoethyl]carbamate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Prepared analogously to Example 82 from 1-acetyl-3-(1-ethoxy-1-phenyl-methylidene)-5-nitro-2-indolinone and 3-tert.butoxycarbonylaminomethylcarbonylaminomethyl-aniline in DMF and subsequent treatment with sodium hydroxide solution in methanol.

Sources & evidence

ORD record
ord-1192152176d5492e9b3719b88a81c5d9
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Reaction notes

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