HCID 25099397, compound → HCID 25099398, compound

HRID 2381992Notes

Reaction equation

HRID 2381992 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]=[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[CH:14]=[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 25099397HCID 25099397, compound

Product 1

HCID 25099398HCID 25099398, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspended solution of 2-pyridin-2-yl-pyrimidine-5-carboxylic acid (2,3-dihydro-indol-1-yl)-amide (0.28 mmol) and MnO2 (1.42 mmol) in DCM (8 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 0-5% methanol in DCM to afford 2-pyridin-2-yl-pyrimidine-5-carboxylic acid indol-1-yl-amide (45 mg, 50%) as a solid. MS: 316 (M+H); 1H NMR (300 MHz, CDCl3): δ 6.48 (s, H), 6.72-7.48 (m, 5H), 7.56 (s, H), 7.88 (s, H), 8.52 (br, 2H), 9.08 (br, 2H), 11.56 (br, N—H). IC50=4.5 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-b43f6e67723a4584bd4b047e970a7bd3
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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