HCID 67103617, compound → HCID 67103616, compound

HRID 390553Notes

Reaction equation

HRID 390553 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:28])[CH2:15][N:16]3[C:20]4=[N:21][CH:22]=[C:23]([N+:25]([O-])=O)[CH:24]=[C:19]4[CH:18]=[N:17]3)[CH2:10][CH2:9]2)=[CH:4][C:3]=1[O:29][CH3:30]>C(O)(=O)C.CCOC(C)=O.[Fe]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:14](=[O:28])[CH2:15][N:16]3[C:20]4=[N:21][CH:22]=[C:23]([NH2:25])[CH:24]=[C:19]4[CH:18]=[N:17]3)[CH2:12][CH2:13]2)=[CH:4][C:3]=1[O:29][CH3:30]

Participants

5

Reactant 1

HCID 67103617HCID 67103617, compound

Product 1

HCID 67103616HCID 67103616, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-(5-nitro-pyrazolo[3,4-b]pyridine-1-yl]ethanone (15 mg) is combined with 200 mg of iron powder in 2 mL of acetic acid at 100° C. for 30 min. After cooling to rt, the reaction solution was diluted with EtOAc and filtered. The filtrate was evaporated in vacuo and purified by HPLC to provide 1-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-(5-amino-pyrazolo[3,4-b]pyridine-1-yl]-ethanone: HPLC retention time=1.46 minutes (Agilent Zorbax SB-C18, 2.1×50 mm, 5μ, 35° C.) using 1 ml/min flow rate, a 2.5 minute gradient of 20% to 100% B with a 1.1 minute wash at 100% B (A=0.1% formic acid/5% acetonitrile/94.9% water, B=0.1% formic acid/5% water/94.9% acetonitrile); MS (ES) M+H expect=414.2. found=415.1.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated in vacuo
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-5a3fdbbac7c44104836cf61d2a42a548
Source dataset
uspto-grants-2013_02
Patent number
US08383630B2

Reaction notes

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