Triphenylphosphine → HCID 66718827, compound

HRID 388230Notes

Reaction equation

HRID 388230 reaction equation
[N:1]1[N:2]2[CH:9]=[C:8]([CH2:10][CH2:11][OH:12])[N:7]=[C:3]2[N:4]=[CH:5][CH:6]=1.O[C:14]1[CH:36]=[CH:35][C:17]2[CH2:18][CH:19]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:20](=[O:28])[N:21]([CH2:23][C:24]([F:27])([F:26])[F:25])[CH2:22][C:16]=2[CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[N:1]1[N:2]2[CH:9]=[C:8]([CH2:10][CH2:11][O:12][C:14]3[CH:36]=[CH:35][C:17]4[CH2:18][CH:19]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:20](=[O:28])[N:21]([CH2:23][C:24]([F:26])([F:27])[F:25])[CH2:22][C:16]=4[CH:15]=3)[N:7]=[C:3]2[N:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 66718803HCID 66718803, compoundHCID 66718917HCID 66718917, compound

Product 1

HCID 66718827HCID 66718827, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 50 mL of a tetrahydrofuran solution containing 0.81 g (4.94 mmol) of 2-(imidazo[1,2-b][1,2,4]triazin-6-yl)ethanol obtained in the same reaction as in Example 3-(a) were added 1.66 g (4.80 mmol) of ethyl 8-hydroxy-3-oxo-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepin-4-acetate (see WO 98/14192A) and 1.76 g (6.71 mmol) of triphenylphosphine, and the mixture was stirred under ice-cooling. Then, 9 mL of a tetrahydrofuran solution containing 1.26 g (6.23 mmol) of diisopropyl azodicarboxylate was added dropwise to the mixture over 45 minutes, the mixture was gradually elevated to room temperature, and stirred for 12 hours.

Workup

  1. customobtained in the same reaction as in Example 3-(a)
  2. temperaturecooling
  3. additionwas added dropwise to the mixture over 45 minutes
  4. customwas gradually elevated to room temperature
  5. stirringstirred for 12 hours

Sources & evidence

ORD record
ord-58b8a6c931f64bfd9427d3f8d86ba49a
Source dataset
uspto-grants-2013_02
Patent number
US08377922B2

Reaction notes

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