Methanol → HCID 178458509, compound

HRID 1046361Notes

Reaction equation

HRID 1046361 reaction equation
[CH:1]([C:4]1[CH:25]=[CH:24][C:7]([C:8]([C:10]2[CH:15]=[C:14]([O:16][CH2:17][C:18]#[CH:19])[CH:13]=[CH:12][C:11]=2[NH:20][CH2:21][C:22]#[N:23])=[O:9])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Sn]([N:39]=[N+:40]=[N-:41])(CCCC)(CCCC)CCCC.[OH-].[K+].CO>C1(C)C=CC=C(C)C=1>[CH:1]([C:4]1[CH:25]=[CH:24][C:7]([C:8]([C:10]2[CH:15]=[C:14]([O:16][CH2:17][C:18]#[CH:19])[CH:13]=[CH:12][C:11]=2[NH:20][CH2:21][C:22]2[NH:41][N:40]=[N:39][N:23]=2)=[O:9])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 4984872Tributyltin azideHCID 59259048HCID 59259048, compound

Product 1

HCID 178458509HCID 178458509, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Procedure

A solution of 0.82 g (2.47 mmol) [2-(4-isopropyl-benzoyl)-4-prop-2-ynyloxy-phenyl-amino]-acetonitrile and 0.8 ml (3.31 mmol) Bu3SnN3 in 20 ml m-xylene is stirred at reflux temperature for 5 h. Then the reaction mixture is cooled to room temperature and 15 ml 2N KOH and 2 ml MeOH are added. This mixture is stirred vigorously for 15 min. After that the phases are separated and to the water layer 4 N HCl is added until a pH ˜1 is reached. The aqueous layer is extracted with dichloromethane/isopropanol=3:1. The combined organic layers are washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting solid is suspended in diethyl ether, stirred for 0.5 h, filtered and dried to afford 0.89 g of the title compound as yellow crystals.

Workup

  1. temperatureat reflux temperature for 5 h
  2. customAfter that the phases are separated and to the water layer 4 N HCl
  3. additionis added until a pH ˜1
  4. extractionThe aqueous layer is extracted with dichloromethane/isopropanol=3:1
  5. washThe combined organic layers are washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. stirringstirred for 0.5 h
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-243b0a8e7ace4b3ea24494767c6bb0ce
Source dataset
uspto-grants-2013_10
Patent number
US08569317B2

Reaction notes

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