HCID 25099273, compound → HCID 25099313, compound

HRID 2381993Notes

Reaction equation

HRID 2381993 reaction equation
[N:1]1([NH:10][C:11]([C:13]2[CH:14]=[N:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)=[N:17][CH:18]=2)=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1>C(Cl)Cl.O=[Mn]=O>[N:1]1([NH:10][C:11]([C:13]2[CH:14]=[N:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)=[N:17][CH:18]=2)=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 1

HCID 25099273HCID 25099273, compound

Product 1

HCID 25099313HCID 25099313, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspended solution of 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid (2,3-dihydro-indol-1-yl)-amide (0.39 mmol) and MnO2 (1.95 mmol) in DCM (10 mL) is stirred at rt for 40 min. The reaction mixture is filtered and the filtrate is concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0-40% EtOAc in heptane to afford 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic indol-1-yl-amide (70 mg, 54%) as a solid. MS: 333 (M+H); 1H NMR (300 MHz, CDCl3): δ 6.60 (s, H), 7.10 (d, H), 7.14-7.46 (m, 4H), 7.50 (br, H), 7.64 (d, H), 8.37 (d, 2H), 8.60-9.40 (br, 3H). IC50=5 nM.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe residue is purified by silica gel chromatography
  4. washeluting with 0-40% EtOAc in heptane

Sources & evidence

ORD record
ord-151fbd3c516c4232a09ee80f67dd4989
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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