Triphenylphosphine → HCID 68707935, compound

HRID 1818841Notes

Reaction equation

HRID 1818841 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][S:11]1(=[O:20])=[O:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:41][CH2:42][N:43]1[CH2:48][CH2:47][N:46]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:45][CH2:44]1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[O:20]=[S:11]1(=[O:19])[N:12]([CH2:41][CH2:42][N:43]2[CH2:48][CH2:47][N:46]([C:49]([O:51][C:52]([CH3:53])([CH3:55])[CH3:54])=[O:50])[CH2:45][CH2:44]2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:10]1[C:3]1[CH:4]=[CH:5][C:6]([F:9])=[C:7]([F:8])[C:2]=1[F:1]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 735736Tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylateHCID 5363146Diisopropyl azodicarboxylateHCID 68710693HCID 68710693, compound

Product 1

HCID 68707935HCID 68707935, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an analogous manner as general VI, a solution of 1-(2,3,4-trifluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole2,2-dioxide (0.21 g, 0.7 mmol) in tetrahydrofuran (10 mL) was cooled to 0° C., treated with triphenylphosphine (0.27 g, 1.0 mmol), tert-Butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate (0.38 g, 1.4 mmol) were added followed by diisopropylazodicarboxylate (0.2 mL, 1.0 mmol to provide tert-butyl 4-{2-[2,2-dioxido-3-(2,3,4-trifluorophenyl)-2,1,3-benzothiadiazol-1(3H)-yl]ethyl}piperazine-1-carboxylate (0.22 g, 625) as white solid:

Workup

  1. additionwere added

Sources & evidence

ORD record
ord-a65ff71090aa4dafbb2ce86d09007574
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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