Triacetoxyperiodinane → HCID 21101726, compound

HRID 1353428Notes

Reaction equation

HRID 1353428 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH:21]4[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]([OH:28])[CH2:22]4)=[O:19])[CH2:14][CH2:13]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH:21]4[CH2:27][CH2:26][CH2:25][CH2:24][C:23](=[O:28])[CH2:22]4)=[O:19])[CH2:14][CH2:13]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 21101724HCID 21101724, compound

Product 1

HCID 21101726HCID 21101726, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(7-chloro-4-quinolinyl)-N-(3-hydroxycycloheptyl)-1-piperazinecarboxamide (300 mg, 0.744 mmol) in CH2Cl2 (20 mL), the Dess-Martin reagent (348 mg, 0.82 mmol) was added at rt. After 3 h, the reaction mixture was quenched with 1 g of Na2S2O3 and 5 mL of NaHCO3 (sat.). The reaction mixture was extracted with CH2Cl2, washed with brine, and dried over Na2SO4. Concentration in vacuo followed by flash chromatography afforded the title product. LC-MS: 401 (M++1). 1H NMR (CDCl3) δ 8.78 (d, 1H), 8.05 (s, 1H), 7.95 (d, 1H), 7.45 (d, 1H), 6.85 (d, 1H), 4.70 (m, 1H), 4.25 (m, 1H), 3.60 (m, 4H), 3.25 (m, 4H), 3.00 (m, 1H), 2.45–2.65 (m, 3H), 1.70–1.90 (m, 6H).

Workup

  1. customthe reaction mixture was quenched with 1 g of Na2S2O3 and 5 mL of NaHCO3 (sat.)
  2. extractionThe reaction mixture was extracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-d404eb0163fa4fb284f190d9d560edd1
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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