Triphenylphosphine → tert-Butyl 4-(4-{2-[(2-oxo-2H-chromen-7-yl)oxy]ethoxy}-1,2,5-thiadiazol-3-yl)-1-piperazinecarboxylate

HRID 1789766Notes

Reaction equation

HRID 1789766 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][CH2:14][CH2:15][O:16][C:17]1[C:18]([N:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)=[N:19][S:20][N:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:55]1[CH:64]=[C:63]2[C:58]([CH:59]=[CH:60][C:61](=[O:65])[O:62]2)=[CH:57][CH:56]=1>C1COCC1>[O:65]=[C:61]1[CH:60]=[CH:59][C:58]2[C:63](=[CH:64][C:55]([O:13][CH2:14][CH2:15][O:16][C:17]3[C:18]([N:22]4[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]4)=[N:19][S:20][N:21]=3)=[CH:56][CH:57]=2)[O:62]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5281426UmbelliferoneHCID 22036393tert-Butyl 4-[4-(2-hydroxyethoxy)-1,2,5-thiadiazol-3-yl]-1-piperazinecarboxylate

Product 1

HCID 22036300tert-Butyl 4-(4-{2-[(2-oxo-2H-chromen-7-yl)oxy]ethoxy}-1,2,5-thiadiazol-3-yl)-1-piperazinecarboxylateYield 123.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (DEAD, 61 μl, 0.39 mmol) was added drop wise to a mixture of the product obtained in Step 2 (100 mg, 0.30 mmol), triphenylphosphine (102 mg, 0.39 mmol) and 7-hydroxycoumarin (63 mg, 0.39 mmol) in dry THF (5 mL). The reaction mixture was stirred at room temperature for 5 days. After solvent removal, the residue was purified by chromatography on silica gel eluting with hexane/EtOAc (1:1) to give the title product as a white solid (176 mg) which had low purity (67% by HPLC). This material was used directly in the following step without further purification.

Workup

  1. customAfter solvent removal
  2. customthe residue was purified by chromatography on silica gel eluting with hexane/EtOAc (1:1)

Sources & evidence

ORD record
ord-98b19d8ee6d64b53b83dce7acbe77625
Source dataset
uspto-grants-2006_07
Patent number
US07071180B2

Reaction notes

Loading…