Hydrochloric Acid → HCID 44192988, compound

HRID 1855346Notes

Reaction equation

HRID 1855346 reaction equation
[Na].[F:2][C:3]([F:11])([C:7]([F:10])([F:9])[F:8])[CH2:4][CH2:5][OH:6].Cl[C:13]1[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]3)=[C:23]([O:33][CH3:34])[CH:22]=2)[N:14]=1.Cl>>[CH3:34][O:33][C:23]1[CH:22]=[C:21]([NH:20][C:15]2[N:16]=[C:17]([CH3:19])[CH:18]=[C:13]([O:6][CH2:5][CH2:4][C:3]([F:11])([F:2])[C:7]([F:10])([F:9])[F:8])[N:14]=2)[CH:26]=[CH:25][C:24]=1[N:27]1[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1086443,3,4,4,4-Pentafluorobutan-1-olHCID 5360545SodiumHCID 57829826HCID 57829826, compound

Product 1

HCID 44192988HCID 44192988, compoundYield 64.5%

Conditions

Temperature
100 °C

Procedure

Sodium (6.9 mg, 0.3 mmol) was dissolved under stirring and heating under an atmosphere of argon in 3,3,4,4,4-pentafluorobutan-1-ol (676 mg, 4.0 mmol). To this solution (4-chloro-6-methyl-pyrimidin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine (66 mg, 0.20 mmol) was added and the reaction mixture was stirred for 16 h at 20° C. and then heated to 100° C. for 4 h. The reaction mixture was poured onto water and was acidified with 1N aqueous hydrochloric acid solution. It was extracted twice with diethyl ether. The aqueous layer was set to basic pH with 1N aqueous sodium hydroxide solution and extracted three times with diethyl ether. The combined organic layers were washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using dichloromethane/methanol (19:1 v/v) as eluent to yield the title compound (59 mg, 64%) as a pale-yellow solid.

Workup

  1. stirringthe reaction mixture was stirred for 16 h at 20° C.
  2. additionThe reaction mixture was poured onto water
  3. extractionIt was extracted twice with diethyl ether
  4. extractionextracted three times with diethyl ether
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-87401b901cdc405f81d1a03ee6d1742f
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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