HCID 25099318, compound → HCID 25099351, compound

HRID 2381996Notes

Reaction equation

HRID 2381996 reaction equation
[N:1]1([NH:10][C:11]([C:13]2[C:14]([CH3:25])=[N:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N: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]([CH3:25])=[N:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N: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 25099318HCID 25099318, compound

Product 1

HCID 25099351HCID 25099351, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspended solution of 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (2,3-dihydro-indol-1-yl)-amide (1.00 mmol) and MnO2 (5.00 mmol) in DCM (10 mL) is stirred at rt for 60 min. The reaction mixture is filtered and the filtrate is concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0-5% methanol in DCM to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid indol-1-ylamide (196 mg, 60%) as a solid. MS: 330 (M+H); 1H NMR (300 MHz, CDCl3): δ 2.77 (s, 3H), 6.58 (s, H), 7.15 (s, 2H), 7.26 (m, 3H), 7.84 (d, H), 8.44 (s, 2H), 8.73 (s, H), 10.94 (br, N—H). 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 0-5% methanol in DCM

Sources & evidence

ORD record
ord-784bce4ba57d443abf03f6020b313f6a
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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