Thiazolidinedione → HCID 59322921, compound

HRID 331237Notes

Reaction equation

HRID 331237 reaction equation
[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]([N:13]2[CH2:18][CH2:17][CH:16]([N:19]4[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[N:21]([CH2:28][CH2:29][CH2:30]O)[C:20]4=[O:32])[CH2:15][CH2:14]2)[CH2:5][CH2:4][CH:3]3[CH2:2]1.[S:33]1[CH2:37][C:36](=[O:38])[NH:35][C:34]1=[O:39].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C1(C)C=CC=CC=1>[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]([N:13]2[CH2:18][CH2:17][CH:16]([N:19]4[C:23]5[CH:22]=[CH:27][CH:26]=[CH:25][C:24]=5[N:21]([CH2:28][CH2:29][CH2:30][N:35]5[C:36](=[O:38])[CH2:37][S:33][C:34]5=[O:39])[C:20]4=[O:32])[CH2:15][CH2:14]2)[CH2:5][CH2:4][CH:3]3[CH2:2]1

Participants

7

Reactant 4

HCID 5437ThiazolidinedioneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 68704028HCID 68704028, compound

Product 1

HCID 59322921HCID 59322921, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

1-[1-(1,2,2a,3,4,5-Hexahydroacenaphthylen-5-yl)piperidin-4-yl]-3-(3-hydroxypropyl)-1,3-dihydro-2H-benzimidazol-2-one and 2,4-thiazolidinedione (314 mg) were dissolved in THF (25 ml), 40% solution (1.22 ml) of triphenylphosphine (702 mg) and diethyl azodicarboxylate (DEAD) in toluene was added, and the mixture was stirred at 50° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (160 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-050d4ec28ac64cbd89a7d7bcbbcbd697
Source dataset
uspto-grants-2014_11
Patent number
US08877779B2

Reaction notes

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