Carbon Tetrachloride → HCID 67779973, compound

HRID 862379Notes

Reaction equation

HRID 862379 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([Cl:28])=[CH:11][C:12]([F:27])=[C:13]([N:15]2[C:24](=[O:25])[N:18]3[CH2:19][CH2:20][CH:21](O)[CH2:22][N:17]3[C:16]2=[O:26])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(Cl)(Cl)[Cl:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:1]([O:8][C:9]1[C:10]([Cl:28])=[CH:11][C:12]([F:27])=[C:13]([N:15]2[C:24](=[O:25])[N:18]3[CH2:19][CH2:20][CH:21]([Cl:30])[CH2:22][N:17]3[C:16]2=[O:26])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 53845504HCID 53845504, compound

Product 1

HCID 67779973HCID 67779973, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 212 mg (0.523 mmol) of 2-(5-benzyloxy-4-chloro-2-fluorophenyl)-5,6,7,8-tetrahydro-6-hydroxy-1H-[1,2,4]triazolo[1,2-α]pyridazine-1,3(2H)-dione (0.523 mmol), 76 μL of CCl4 (0.784 mmol), and 206 mg of triphenylphosphine (0.784 mmol) in 8 mL of dichloromethane was warmed under reflux for 2h. The mixture was then concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel, eluting with a 1: 1 v:v mixture of ethyl acetate and n-hexane to give 200 mg of the title product of Step C, a compound of the invention, as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 2.3 (m, 2H), 3.5 (m, 2H), 3.9 (m, 2H), 4.4 (m, 1H), 5.1 (s, 2H), 7.0 (d, 1H), 7.4 (m, 6H).

Workup

  1. temperaturewas warmed
  2. temperatureunder reflux for 2h
  3. concentrationThe mixture was then concentrated under reduced pressure
  4. customThe crude product was purified by flash chromatography over silica gel
  5. washeluting with a 1: 1 v
  6. additionv mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-00c69a1ba86b416c81c7aba47f5cb818
Source dataset
uspto-grants-1998_02
Patent number
US05719104

Reaction notes

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