Diethyl Ether → HCID 86686810, compound

HRID 1403164Notes

Reaction equation

HRID 1403164 reaction equation
[F:1][CH:2]([F:41])[C:3]1[N:7]([C:8]2[CH:13]=[C:12]([N:14]3CCOCC3)[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]4C(OC)=O)[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.[O:42]1[CH2:46][CH2:45]CC1.[CH3:47][Li].[Cl-].[NH4+].[CH2:51]([O:53][CH2:54][CH3:55])[CH3:52]>>[F:1][CH:2]([F:41])[C:3]1[N:7]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:55][CH2:54][O:53][CH2:51][CH2:52]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:46]([OH:42])([CH3:45])[CH3:47])[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

6

Reactant 5

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 86686811HCID 86686811, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 86686810HCID 86686810, compound

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 1.06 M solution of methyllithium in diethyl ether (0.33 mL) at 0° C., followed by stirring at the same temperature for 4 hours. To the reaction mixture was added a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by amino silica gel column chromatography (hexane:ethyl acetate) to obtain 2-(2-{4-[({4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(morpholin-4-yl)pyrimidin-2-yl}amino)methyl]piperidin-1-yl}cyclopentyl)propan-2-ol (11.1 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by amino silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-9c23fd257935456a878897a9c2cba798
Source dataset
uspto-grants-2014_12
Patent number
US08912180B2

Reaction notes

Loading…