HCID 21106579, compound → HCID 178428367, compound

HRID 1765390Notes

Reaction equation

HRID 1765390 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[N:9]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=1)[N:8]=[C:7]2[NH:25][C:26]1[N:27](C(C)(C)C)[N:28]=[C:29]([CH3:31])[CH:30]=1)([O-:3])=[O:2]>C(O)=O>[C:21]([C:18]1[CH:19]=[CH:20][C:15]([N:9]2[N:8]=[C:7]([NH:25][C:26]3[NH:27][N:28]=[C:29]([CH3:31])[CH:30]=3)[C:6]3[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[C:10]2=[O:14])=[CH:16][CH:17]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

3

Reactant 1

HCID 21106579HCID 21106579, compound

Product 1

HCID 178428367HCID 178428367, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

12 mg 6-Nitro-4-(2-tert-butyl-5-methyl-2H-pyrazol-3-ylamino)-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one (preparation see ZB-1) were deprotected by heating in formic acid as described for ZB-1. Evaporation of excess formic acid and chromatography of the residue on silica, eluting with dichloromethane and then with dichloromethane/methanol 20:1 gave 5 mg of the title product. 1H-NMR: (400 MHz, D6-DMSO) 11.9 (1H, br s), 9.78 (1H, s), 9.52 (1H, s), 8.65–8.56 (2H, m), 7.65 (2H, d), 7.53 (2H, d), 6.26 (1H, s), 2.20 (3H, s), 1.35 (9H, s); MS (ESI+)=418.32 (M+H)+.

Workup

  1. customEvaporation of excess formic acid and chromatography of the residue on silica
  2. washeluting with dichloromethane

Sources & evidence

ORD record
ord-4ecbf53afdc34dcb947f4cbbafcdeca0
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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