Water → HCID 178513607, compound

HRID 474483Notes

Reaction equation

HRID 474483 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:9]([NH:11][C:12]3[CH:13]=[C:14]([CH:18]([NH:22][C:23]4[C:32]5[C:27](=[C:28]([C:33]([NH2:35])=[O:34])[CH:29]=[CH:30][CH:31]=5)[N:26]=[CH:25][N:24]=4)[CH2:19][CH2:20][OH:21])[CH:15]=[CH:16][CH:17]=3)=[O:10])[NH:7][N:8]=2)[CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.O.[OH-].[Na+]>CS(C)=O.ClCCl>[CH:1]1([C:4]2[CH:5]=[C:6]([C:9]([NH:11][C:12]3[CH:13]=[C:14]([CH:18]([NH:22][C:23]4[C:32]5[C:27](=[C:28]([C:33]([NH2:35])=[O:34])[CH:29]=[CH:30][CH:31]=5)[N:26]=[CH:25][N:24]=4)[CH2:19][CH:20]=[O:21])[CH:15]=[CH:16][CH:17]=3)=[O:10])[NH:7][N:8]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 178513608HCID 178513608, compound

Product 1

HCID 178513607HCID 178513607, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

227 mg (0.46 mmol) 4-(1-{3-[(5-Cyclopropyl-2H-pyrazole-3-carbonyl)-amino]-phenyl}-3-hydroxy-propylamino)-quinazoline-8-carboxylic acid amide were dissolved in 2.5 ml DMSO and 1.98 ml (0.59 mmol) 0.3 M Dess-Martin Periodane in dichloromethane wee added to the mixture. The mixture was stirred for 2 h at room temperature, 20 ml water and 2 ml 1N NaOH were added and the precipitate was filtered, washed with water and dried in vacuo. 245 mg, off-white solid.

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-237f5480414940c29f9b7cf7ff9cc5d4
Source dataset
uspto-grants-2014_01
Patent number
US08637532B2

Reaction notes

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