HCID 25099314, compound → HCID 25099317, compound

HRID 2381995Notes

Reaction equation

HRID 2381995 reaction equation
[N:1]1([NH:10][C:11]([C:13]2[C:14]([CH3:26])=[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[C:14]([CH3:26])=[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 25099314HCID 25099314, compound

Product 1

HCID 25099317HCID 25099317, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspended solution of 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (2,3-dihydro-indol-1-yl)-amide (0.72 mmol) and MnO2 (3.60 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)-4-methyl-pyrimidine-5-carboxylic acid indol-1-ylamide (185 mg, 75%) as a solid. MS: 347 (M+H); 1H NMR (300 MHz, CDCl3): δ 2.73 (s, 3H), 6.53 (s, H), 7.03 (d, H), 7.08-7.36 (m, 4H), 7.37-7.75 (m, 2H), 8.04-8.40 (m, 2H), 8.56 (br, H), 8.81 (br, H). IC50=10 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-8395f82715744ab385324221ed66fbcb
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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