Dimethylformamide → HCID 11725593, compound

HRID 1295687Notes

Reaction equation

HRID 1295687 reaction equation
CN(C)C=O.C(OC([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[C:20]([O:25]CCO)=[N:21][CH:22]=[CH:23][N:24]=2)[CH2:15][CH2:14]1)=O)(C)(C)C.[C:29]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:30]=1.[Cl:48][C:49]1[CH:54]=[CH:53][C:52]([OH:55])=[C:51]([F:56])[CH:50]=1>C1COCC1>[Cl:48][C:49]1[CH:54]=[CH:53][C:52]([O:55][CH2:29][CH2:30][N:21]2[CH:22]=[CH:23][N:24]=[C:19]([N:16]3[CH2:15][CH2:14][NH:13][CH2:18][CH2:17]3)[C:20]2=[O:25])=[C:51]([F:56])[CH:50]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 1819754-Chloro-2-fluorophenolHCID 114160742-[3-(4-Tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol

Product 1

HCID 11725593HCID 11725593, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1′-Azobis(N,N-dimethylformamide (TMAD; 0.217 g, 1.26 mmol) was added to a stirred mixture of 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-pyrazinyloxy]ethanol (0.324 g, 1.00 mmol), triphenylphosphine (0.324 g, 1.23 mmol) and 4-chloro-fluorophenol (0.217 g, 1.48 mmol) in THF (1 mL) at room temperature. After 2 h, the reaction mixture was concentrated and the crude N-t-BOC derivative of the title compound was N-deprotected with TFA/dichloromethane/H2O (45:50:5). Purification by chromatography on silica gel using EtOAc/toluene (4:6) as eluent gave 0.123 g (35%) of the title compound as a yellow oil. HRMS m/z calcd for C16H18ClFN4O2 (M)+ 352.1102, found 352.1098.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-67f13a88ed534e90bd26e851c6ac8e85
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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