Sodium Hydroxide → tert-butyl N-[2-[4-[[(Z)-(5-nitro-2-oxo-1H-indol-3-ylidene)-phenylmethyl]amino]phenyl]ethyl]carbamate

HRID 24840Notes

Reaction equation

HRID 24840 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(OC(N[CH:35]([C:37]1[CH:43]=[CH:42][C:40]([NH2:41])=[CH:39][CH:38]=1)[CH3:36])=O)(C)(C)C.[OH-:44].[Na+]>CN(C=O)C.CO>[C:7]([O:44][C:5]([NH:4][CH2:36][CH2:35][C:37]1[CH:38]=[CH:39][C:40]([NH:41]/[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:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:42][CH:43]=1)=[O:26])([CH3:12])([CH3:8])[CH3:6]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 22569414tert-butyl N-[1-(4-aminophenyl)ethyl]carbamateHCID 542801041-Acetyl-3-{1-ethoxy-1-phenylmethylidene}-5-nitro-2-indolinone

Product 1

HCID 178453288tert-butyl N-[2-[4-[[(Z)-(5-nitro-2-oxo-1H-indol-3-ylidene)-phenylmethyl]amino]phenyl]ethyl]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 4-(1-tert.butoxycarbonylamino-ethyl)-aniline in DMF and subsequent treatment with sodium hydroxide solution in methanol.

Sources & evidence

ORD record
ord-45412eef057e46c8a137a148f2a7089d
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Reaction notes

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