HCID 22644641, compound → HCID 22644631, compound

HRID 2414345Notes

Reaction equation

HRID 2414345 reaction equation
[O:1]=[C:2]1[O:7][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]1[CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:30]=[CH:29][C:21]([C:22](OC(C)(C)C)=[O:23])=[CH:20][CH:19]=2)[CH2:14][CH2:13]1>FC(F)(F)C(O)=O.ClCCl>[CH3:5][CH:4]([NH:3][C:22](=[O:23])[C:21]1[CH:29]=[CH:30][C:18]([N:15]2[CH2:14][CH2:13][CH:12]([N:3]3[C:4]4[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=4[CH2:6][O:7][C:2]3=[O:1])[CH2:17][CH2:16]2)=[CH:19][CH:20]=1)[CH3:11]

Participants

4

Reactant 1

HCID 22644641HCID 22644641, compound

Product 1

HCID 22644631HCID 22644631, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the product from step (i) (0.29 g) in a mixture of trifluoroacetic acid (10 ml) and dichloromethane (10 ml) was stirred at room temperature for 1 h. The solution was evaporated under reduced pressure, the residue dissolved in N,N-dimethylformamide then bromo-tris-pyyrolidino-phosphonium hexafluorophosphate (0.16 g), isopropylamine (0.06 ml) and N,N-diisopropylethylamine (0.06 ml) added. The solution was stirred at room temperature for 16 h then evaporated under reduced pressure. Purification was by chromatography eluting with (1:5) ethyl acetate/dichloromethane. Yield 0.01 g as a solid.

Workup

  1. customThe solution was evaporated under reduced pressure
  2. dissolutionthe residue dissolved in N,N-dimethylformamide
  3. additionbromo-tris-pyyrolidino-phosphonium hexafluorophosphate (0.16 g), isopropylamine (0.06 ml) and N,N-diisopropylethylamine (0.06 ml) added
  4. stirringThe solution was stirred at room temperature for 16 h
  5. customthen evaporated under reduced pressure
  6. customPurification
  7. washeluting with (1:5) ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-1d5ee9217bd44b08b4d0457cf5ddca2b
Source dataset
uspto-grants-2004_11
Patent number
US06812226B2

Reaction notes

Loading…