Triethylamine → HCID 67960479, compound

HRID 509602Notes

Reaction equation

HRID 509602 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-07062bf2db764fdda87c8606ebb49a82
Source dataset
uspto-grants-2015_08
Patent number
US09096587B2

Reaction notes

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