Pyridine → HCID 86684835, compound

HRID 2402606Notes

Reaction equation

HRID 2402606 reaction equation
[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([NH2:23])[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][N:4]=[N:3]1.N1C=CC=CC=1.[O:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[CH2:32][CH:31]1[C:39](Cl)=[O:40]>ClCCl>[CH3:1][N:2]1[C:6]([C:7](=[N:14][O:15][CH2:16][C:17]2[N:22]=[C:21]([NH:23][C:39]([CH:31]3[CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[O:30]3)=[O:40])[CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27954272,3-dihydro-1-benzofuran-2-carbonyl chlorideHCID 768322206-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine

Product 1

HCID 86684835HCID 86684835, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine (100 mg, 0.32 mmol) in dry dichloromethane (4 mL) under argon was added pyridine (39 μL, 0.48 mmol) at room temperature, followed after fifteen minutes by 2,3-dihydro-1-benzofuran-2-carbonyl chloride (88 mg, 0.48 mmol). The reaction mixture was stirred overnight at room temperature and quenched by filtration on bi-layer cartridge filled with 1.4 g of basic alumina and 1 g of silica. The cartridge was rinsed twice by 10 mL of dichloromethane. The combined filtrated solutions were evaporated in vacuo to yield a colorless oil. Purification on silica gel afforded of N-{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}-2,3-dihydro-1-benzofuran-2-carboxamide as a colorless oil [150 mg, yield 96%; HPLC/MS: nm/z=456 (M+H); log P(HCOOH)=3.67].

Workup

  1. customquenched by filtration on bi-layer cartridge
  2. additionfilled with 1.4 g of basic alumina and 1 g of silica
  3. washThe cartridge was rinsed twice by 10 mL of dichloromethane
  4. filtrationThe combined filtrated solutions
  5. customwere evaporated in vacuo
  6. customto yield a colorless oil
  7. customPurification on silica gel

Sources & evidence

ORD record
ord-9c0ba3b891934eb4ad6e3eae2816a6ff
Source dataset
uspto-grants-2014_08
Patent number
US08796463B2

Reaction notes

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