Triacetoxyperiodinane → HCID 11341642, compound

HRID 2099758Notes

Reaction equation

HRID 2099758 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH2:30][C:31]2[CH:32]=[C:33]3[C:37](=[C:38]([CH3:40])[CH:39]=2)[NH:36][N:35]=[CH:34]3)[CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][C:20]3=[O:29])[CH2:15][CH2:14]2)=[O:12])=[N:7][CH:8]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:40][C:38]1[CH:39]=[C:31]([CH2:30][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([CH:2]=[O:1])=[CH:8][N:7]=2)[CH2:10][C:11](=[O:12])[N:13]2[CH2:14][CH2:15][CH:16]([N:19]3[CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][C:20]3=[O:29])[CH2:17][CH2:18]2)[CH:32]=[C:33]2[C:37]=1[NH:36][N:35]=[CH:34]2

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 11753024HCID 11753024, compound

Product 1

HCID 11341642HCID 11341642, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid (±)-3-(1-(3-(5-(hydroxymethyl)pyridin-2-yl)-4-(7-methyl-1H-indazol-5-yl)butanoyl)piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one (20.9 mg, 0.025 mmol, 1.0 equiv) and Dess-Martin reagent (21.8 mg, 2.0 equiv) were dissolved in anhydrous methylene chloride (2 mL). The cloudy solution was stirred at room temperature for 1 h. The reaction was quenched with 0.5 N sodium hydroxide. The layers were separated and the organic layer was washed with brine, dried over sodium sulfate and concentrated to give an off-white solid. Purification by flash column chromatography (10% MeOH in methylene chloride) afforded the desired product (9.5 mg, 69%) as a colorless oily solid. 1H-NMR (400 MHz, CDCl3) δ 10.02 (d, J=8.0 Hz, 1H), 9.06 (d, J=16.4 Hz, 1H), 7.94-7.82 (m, 2H), 7.18-7.08 (m, 4H), 7.08-6.84 (m, 3H), 6.65 (d, J=7.6 Hz, 1H), 4.68-4.44 (m, 2H), 4.24, 4.16 (2s, 1H), 4.05-3.95 (m, 1H), 3.88-3.76 (br. 1H), 3.30-2.92 (m, 4H), 2.72-2.47 (m, 2H), 2.47 (s, 3H), 1.84-1.35 (m, 6H).

Workup

  1. customThe reaction was quenched with 0.5 N sodium hydroxide
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto give an off-white solid
  7. customPurification by flash column chromatography (10% MeOH in methylene chloride)

Sources & evidence

ORD record
ord-eaae28a8e72844da8fb7ccd83a03d970
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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