Iodoethane → HCID 71737886, compound

HRID 518898Notes

Reaction equation

HRID 518898 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].ICC.Cl.N1CC[CH:15]([C:18]2[CH:22]=[C:21]([NH:23][C:24]3[N:25]=[CH:26][C:27]4[S:32][C:31]([C:33]([NH2:35])=[O:34])=[C:30]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=5[O:42][C:43]([F:46])([F:45])[F:44])[C:28]=4[N:29]=3)[N:20]([CH:47]([CH3:49])[CH3:48])[N:19]=2)CC1>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([N:3]1[CH2:6][CH2:7][CH:15]([C:18]2[CH:22]=[C:21]([NH:23][C:24]3[N:25]=[CH:26][C:27]4[S:32][C:31]([C:33]([NH2:35])=[O:34])=[C:30]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=5[O:42][C:43]([F:46])([F:44])[F:45])[C:28]=4[N:29]=3)[N:20]([CH:47]([CH3:49])[CH3:48])[N:19]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 6340Iodoethane3×HCID 8471Triethylamine3×HCID 86698046HCID 86698046, compound

Product 1

HCID 71737886HCID 71737886, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

70 microliters of triethylamine and 17 microliters of iodoethane are added, at a temperature of about 20° C., to a solution of 100 mg of 2-{[3-(piperidin-4-yl)-1-(propan-2-yl)-1H-pyrazol-5-yl]amino}-7-[2-(trifluoromethoxy)phenyl]thieno[3,2-d]pyrimidine-6-carboxamide hydrochloride in 2.5 ml of DMF under an argon atmosphere, and the mixture is left to stir for 4 h. 70 microliters of triethylamine and 10 microliters of iodoethane are then added and then, after stirring for 15 h, a further addition of 70 microliters of triethylamine and 10 microliters of iodoethane is carried out and the mixture is left to stir for a further 24 hours. The reaction medium is diluted with 40 ml of ethyl acetate and then the organic phase is washed three times with 15 ml of water. The aqueous phase is extracted twice with 20 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and concentrated under vacuum, so as to obtain a yellow solid. The crude product is purified by flash chromatography on silica gel, elution being carried out with a dichloromethane/methanol/NH4OH (96/4/0.1%) mixture, so as to obtain 57 mg of 2-{[3-(1-ethylpiperidin-4-yl)-1-(propan-2-yl)-1H-pyrazol-5-yl]amino}-7-[2-(trifluoromethoxy)phenyl]thieno[3,2-d]pyrimidine-6-carboxamide in the form of a yellow solid.

Workup

  1. waitthe mixture is left
  2. stirringafter stirring for 15 h
  3. waitthe mixture is left
  4. stirringto stir for a further 24 hours
  5. washthe organic phase is washed three times with 15 ml of water
  6. extractionThe aqueous phase is extracted twice with 20 ml of ethyl acetate
  7. dry with materialThe combined organic phases are dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customso as to obtain a yellow solid
  11. customThe crude product is purified by flash chromatography on silica gel, elution

Sources & evidence

ORD record
ord-ff940cf746e942899bc8b8c147de09fc
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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