HCID 86606003, compound → HCID 68681503, compound

HRID 901053Notes

Reaction equation

HRID 901053 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])[CH:5]=[CH:4][C:3]=1[CH:15]([N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[C:20]1=[O:28])[C:16]([NH2:18])=[O:17]>C(O)(=O)C.[Zn]>[NH2:25][C:21]1[C:20](=[O:28])[N:19]([CH:15]([C:3]2[CH:4]=[CH:5][C:6]([N:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]3=[O:14])=[CH:7][C:2]=2[F:1])[C:16]([NH2:18])=[O:17])[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 1

HCID 86606003HCID 86606003, compound

Product 1

HCID 68681503HCID 68681503, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

64.3 A suspension of 60 mg [2-fluoro-4-(2-oxo-pyridin-1-yl)-phenyl]-2-(3-nitro-2-oxo-pyridin-1-yl)-acetamide in 1 ml acetic acid was treated portionwise with 82 mg activated zinc powder. The reaction mixture was stirred for 3 hrs at r.t. The solid was filtered off and washed carefully with EtOH. The filtrate was concentrated. The crude product was purified by chromatography (silica, gradient CH2Cl2->CH2Cl2/MeOH 95:5) to give 39 mg 2-(3-amino-2-oxo-pyridin-1-yl)-[2-fluoro-4-(2-oxo-pyridin-1-yl)-phenyl]-acetamide as off-white solid. MS 355.0 ([M+H]+)

Workup

  1. additionwas treated portionwise with 82 mg
  2. filtrationThe solid was filtered off
  3. washwashed carefully with EtOH
  4. concentrationThe filtrate was concentrated
  5. customThe crude product was purified by chromatography (silica, gradient CH2Cl2->CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-c1c8736bd22e434c86034cfbed6f97e4
Source dataset
uspto-grants-2008_04
Patent number
US07361672B2

Reaction notes

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