Triphenylphosphine → HCID 118598893, compound

HRID 1050411Notes

Reaction equation

HRID 1050411 reaction equation
[CH2:1]([N:8]([CH2:20][CH2:21][CH2:22]O)[C:9]([C:11]1[NH:12][C:13](=[O:19])[C:14]([Br:18])=[CH:15][C:16]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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>[CH2:1]([N:8]1[CH2:20][CH2:21][CH2:22][N:12]2[C:13](=[O:19])[C:14]([Br:18])=[CH:15][C:16]([CH3:17])=[C:11]2[C:9]1=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 118598811HCID 118598811, compound

Product 1

HCID 118598893HCID 118598893, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-benzyl-5-bromo-N-(3-hydroxypropyl)-3-methyl-6-oxo-1,6-dihydropyridine-2-carboxamide (5, 1.5 g, 3.9 mmol) in tetrahydrofuran (30 mL), triphenylphosphine (1.5 g, 5.9 mmol) and diisopropyl azodicarboxylate (1.2 g, 5.9 mmol) were added at 0° C. The mixture was stirred at room temperature for 16 h. After completion, solvent was removed under reduced pressure and the crude was purified by flash chromatography eluting with 40% ethyl acetate in hexane. Appropriate fractions were concentrated under reduced pressure to afford 2-benzyl-8-bromo-10-methyl-2,3,4,5-tetrahydropyrido[1,2-a][1,4]diazepine-1,7-dione (6) as yellow solid. Yield: 0.9 g, 64%; MS (ESI) m/z 361.18 [M+1]+.

Workup

  1. customAfter completion, solvent was removed under reduced pressure
  2. customthe crude was purified by flash chromatography
  3. washeluting with 40% ethyl acetate in hexane
  4. concentrationAppropriate fractions were concentrated under reduced pressure

Sources & evidence

ORD record
ord-89f6cca1562846b4af6e790cd13908ab
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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