Triethylamine → HCID 67960479, compound

HRID 1478127Notes

Reaction equation

HRID 1478127 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[N:13]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][N:19]=2)=[N:16][N:15]=[C:14]1/[CH:28]=[CH:29]/[C:30]([NH:32][NH:33][C:34]([C:36]1[CH:41]=[CH:40][N:39]=[C:38]([O:42][CH3:43])[CH:37]=1)=O)=[O:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)Br.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:10])([F:12])[F:11])[CH:5]=[CH:4][C:3]=1[N:13]1[C:14](/[CH:28]=[CH:29]/[C:30]2[O:31][C:34]([C:36]3[CH:41]=[CH:40][N:39]=[C:38]([O:42][CH3:43])[CH:37]=3)=[N:33][N:32]=2)=[N:15][N:16]=[C:17]1[C:18]1[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:25])=[O:26])=[CH:20][N:19]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67960383HCID 67960383, compound

Product 1

HCID 67960479HCID 67960479, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N′-[(E)-3-[4-(2-chloro-4-trifluoromethoxyphenyl)-5-(5-methylsulfonyl-2-pyridyl)-1,2,4-triazol-3-yl]prop-2-enoyl]-2-methoxy-pyridine-4-carbohydrazide was dissolved into dichloromethane (10 mL), and triphenylphosphine (0.19 g, 0.736 mmol), carbon tetrabromide (0.24 g, 0.736 mmol) and triethylamine (0.18 mL, 1.30 mmol) was added. The reaction mixture was kept at ambient temperature for 2 h. The final compound was purified by column chromatography (eluting with hexane and ethyl acetate 1:3) to give 2-(4-(2-chloro-4-trifluoromethoxyphenyl)-5-((E)-2-(5-(2-methoxypyridin-4-yl)-1,3,4-oxadiazol-2-yl)vinyl)-4H-1,2,4-triazol-3-yl)-5-(methylsulfonyl)pyridine as a yellow solid. Yield: 0.07 g, 30%.

Workup

  1. additionwas added
  2. customThe final compound was purified by column chromatography (eluting with hexane and ethyl acetate 1:3)

Sources & evidence

ORD record
ord-2f25d950c8514fb78140a84ed7412304
Source dataset
uspto-grants-2016_08
Patent number
US09403812B2

Reaction notes

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