Triacetoxyperiodinane → HCID 11364682, compound

HRID 2099773Notes

Reaction equation

HRID 2099773 reaction equation
[O:1]=[C:2]1[N:11]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH:21]([C:33]3[CH:38]=[C:37]([CH2:39][OH:40])[CH:36]=[CH:35][N:34]=3)[CH2:22][C:23]3[CH:24]=[C:25]4[C:29](=[C:30]([CH3:32])[CH:31]=3)[NH:28][N:27]=[CH:26]4)=[O:19])[CH2:14][CH2:13]2)[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]=[C:2]1[N:11]([CH:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][CH:21]([C:33]3[CH:38]=[C:37]([CH:39]=[O:40])[CH:36]=[CH:35][N:34]=3)[CH2:22][C:23]3[CH:24]=[C:25]4[C:29](=[C:30]([CH3:32])[CH:31]=3)[NH:28][N:27]=[CH:26]4)=[O:19])[CH2:16][CH2:17]2)[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 11387141HCID 11387141, compound

Product 1

HCID 11364682HCID 11364682, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To solid (±)-1-(4-(hydroxymethyl)pyridin-2-yl)-2-(7-methyl-1H-indazol-5-yl)ethyl 4-(2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidine-1-carboxylate (28 mg, 0.0518 mmol, 1.0 equiv) was added Dess-Martin reagent (44 mg, 0.104 mmol, 2.0 equiv) and anhydrous methylene chloride (4 mL). The cloudy solution was stirred at room temperature for 2 h. The reaction was quenched with 0.5 N sodium hydroxide. The layers were separated and the organic layer was washed with brine, dried and concentrated to give an off-white solid. Purification by flash column chromatography (10% methanol/methylene chloride) afforded the desired product (23 mg, 82.4%) as an off-white powder. MS (ESI) [M+Na]+=559. 1H-NMR (400 MHz, CDCl3) δ 10.02 (s, 1H), 8.88 (d, J=3.2 Hz, 1H), 7.97 (s, 1H), 7.70-7.40 (m, 3H), 7.26-6.75 (m, 5H), 6.67 (br., 1H), 6.13-5.90 (m, 1H), 4.65-3.75 (m, 4H), 3.50-3.10 (m, 3H), 3.10-2.68 (m, 2H), 2.50 (s, 3H), 1.95-1.38 (m, 5H). HPLC tR=1.59 min.

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. customdried
  5. concentrationconcentrated
  6. customto give an off-white solid
  7. customPurification by flash column chromatography (10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-48914829e53d41fc9946613fc6bfabb8
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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