Tetrahydrofuran → HCID 86686814, compound

HRID 1403167Notes

Reaction equation

HRID 1403167 reaction equation
[F:1][CH:2]([F:41])[C:3]1[N:7]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([NH:20][CH2:21][CH:22]3[CH2:27][CH2:26][N:25]([CH:28]4[CH2:32][CH2:31][CH2:30][CH:29]4[C:33](OC)=[O:34])[CH2:24][CH2:23]3)[N:9]=2)[C:6]2[CH:37]=[CH:38][CH:39]=[CH:40][C:5]=2[N:4]=1.O1CCCC1.C([Al]CC(C)C)C(C)C.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CO>[F:41][CH:2]([F:1])[C:3]1[N:7]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[N:11]=[C:10]([NH:20][CH2:21][CH:22]3[CH2:27][CH2:26][N:25]([CH:28]4[CH2:32][CH2:31][CH2:30][CH:29]4[CH2:33][OH:34])[CH2:24][CH2:23]3)[N:9]=2)[C:6]2[CH:37]=[CH:38][CH:39]=[CH:40][C:5]=2[N:4]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 62649Sodium sulfate decahydrateHCID 16682954DibahHCID 86686811HCID 86686811, compound

Product 1

HCID 86686814HCID 86686814, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a mixture of methyl 2-{-4-[({4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(morpholin-4-yl)pyrimidin-2-yl}amino)methyl]piperidin-1-yl}cyclopentane carboxylate (50 mg) and tetrahydrofuran (1 mL) were added a 1.01 M solution of (240 μL) diisobutylaluminum in toluene at 0° C., followed by stirring at the same temperature for 6 hours. To the reaction mixture were added methanol and sodium sulfate decahydrate, followed by stirring at room temperature for 1 hour. The insoluble matter was removed by filtration and then concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50-0:100) to obtain desired (2-{4-[({4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(morpholin-4-yl)pyrimidin-2-yl}amino)methyl]piperidin-1-yl}cyclopentyl)methanol (33 mg).

Workup

  1. stirringby stirring at room temperature for 1 hour
  2. customThe insoluble matter was removed by filtration
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50-0:100)

Sources & evidence

ORD record
ord-36192032a6df424aa6dec4992c451f88
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

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