Triphenylphosphine → 2-(2,6-Difluorophenoxy)ethyl 3-(1-piperazinyl)-2-pyrazinyl ether

HRID 493290Notes

Reaction equation

HRID 493290 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[OH:9].CN(C(/N=N/C(N(C)C)=O)=O)C.C(OC([N:29]1[CH2:34][CH2:33][N:32]([C:35]2[C:36]([O:41][CH2:42][CH2:43]O)=[N:37][CH:38]=[CH:39][N:40]=2)[CH2:31][CH2:30]1)=O)(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[N:32]1([C:35]2[C:36]([O:41][CH2:42][CH2:43][O:9][C:3]3[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=3[F:8])=[N:37][CH:38]=[CH:39][N:40]=2)[CH2:33][CH2:34][NH:29][CH2:30][CH2:31]1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 943922,6-DifluorophenolHCID 5353800DiamideHCID 114160742-[3-(4-Tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol

Product 1

HCID 220363682-(2,6-Difluorophenoxy)ethyl 3-(1-piperazinyl)-2-pyrazinyl ether

Procedure

The title compound was prepared according to the procedure of Example 77 starting from 2,6-difluorophenol (239 mg, 1.84 mmol), TMAD (384 mg, 2.25 mmol), 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol (600 mg, 1.86 mmol; prepared in Example 52, Step 2), and triphenylphosphine (969 mg, 3.69 mmol) to give 279 mg (45%) of a solid: mp 101-102° C. HRMS m/z calcd for C16H18F2N4O2 (M)+336.1398, found 336.1403.

Sources & evidence

ORD record
ord-92a83ca3dbf3448b96d6300593765a0f
Source dataset
uspto-grants-2009_05
Patent number
US07534794B2

Reaction notes

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