Dimethylformamide → HCID 86651628, compound

HRID 57705Notes

Reaction equation

HRID 57705 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([NH:20][CH2:21][CH2:22][NH:23][C:24]2[N:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)[C:12]2[N:13]([N:15]=[C:16]([CH2:18][OH:19])[CH:17]=2)[CH:14]=1.COCCOC.CN(C=O)C.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([NH:20][CH2:21][CH2:22][NH:23][C:24]2[N:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)[C:12]2[N:13]([N:15]=[C:16]([CH:18]=[O:19])[CH:17]=2)[CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 80711,2-DimethoxyethaneHCID 159087TriacetoxyperiodinaneHCID 58170042HCID 58170042, compound

Product 1

HCID 86651628HCID 86651628, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1.2 g (2.64 mmol) of 6-[(2-{[6-(2,4-dichlorophenyl)-2-(hydroxymethyl)pyrazolo[1,5-a]pyrazin-4-yl]amino}ethyl)amino]pyridine-3-carbonitrile (Example 42) were suspended in 80 ml of dichloromethane (shaken with water beforehand). 80 ml of 1,2-dimethoxyethane and 40 ml of DMF were then added, and the mixture was cooled to 0° C. 2.46 g (5.81 mmol) of Dess-Martin periodinane were added, ice-bath cooling was removed and the mixture was stirred at RT for 2 h. Ethyl acetate was added, and the mixture was washed first with a 10% strength sodium thiosulfate solution and then with saturated aqueous sodium bicarbonate solution. Drying of the organic phase with sodium sulfate and removal of the solvent under reduced pressure gave 1.2 g (94% of theory) of the product as a solid which was reacted without further purification.

Workup

  1. temperatureice-bath cooling
  2. customwas removed
  3. additionEthyl acetate was added
  4. washthe mixture was washed first with a 10% strength sodium thiosulfate solution
  5. dry with materialDrying of the organic phase with sodium sulfate and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-ce32767070b9493d8880a9b418adbe53
Source dataset
uspto-grants-2016_09
Patent number
US09434731B2

Reaction notes

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