HCID 25099395, compound → HCID 25099316, compound

HRID 2381994Notes

Reaction equation

HRID 2381994 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[NH:11][C:12]([C:14]1[CH:15]=[N:16][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[N:18][CH:19]=1)=[O:13]>C(Cl)Cl.O=[Mn]=O>[CH3:1][C:2]1[N:3]([NH:11][C:12]([C:14]2[CH:15]=[N:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)=[N:18][CH:19]=2)=[O:13])[C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 1

HCID 25099395HCID 25099395, compound

Product 1

HCID 25099316HCID 25099316, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspended solution of 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid (2-methyl-2,3-dihydro-indol-1-yl)-amide (0.98 mmol) and MnO2 (4.88 mmol) in DCM (15 mL) is stirred at rt for 2 h. 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 acid (2-methyl-indol-1-yl)-amide (230 mg, 97%) as a solid. MS: 347 (M+H); 1H NMR (300 MHz, CDCl3): δ 2.08-2.40 (m, 3H), 6.27 (s, H), 6.95-7.35 (m, 4H), 7.36-7.65 (m, 2H), 8.20-8.44 (m, 2H), 8.49-9.20 (d, 2H). IC50=6 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-ad835e8b9656481e9a7c818bf2ea3742
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

Loading…