Water → HCID 67200711, compound

HRID 509975Notes

Reaction equation

HRID 509975 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=[C:13]3[C:12]([CH2:21][C:22]3[CH:23]=[N:24][C:25]([NH:28][CH2:29][C:30]4[C:31]([O:37][CH3:38])=[N:32][CH:33]=[C:34]([F:36])[CH:35]=4)=[N:26][CH:27]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[F:36][C:34]1[CH:35]=[C:30]([CH2:29][NH:28][C:25]2[N:26]=[CH:27][C:22]([CH2:21][C:12]3[C:13]4[C:14](=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=4)[NH:10][CH:11]=3)=[CH:23][N:24]=2)[C:31]([O:37][CH3:38])=[N:32][CH:33]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 67200202HCID 67200202, compound

Product 1

HCID 67200711HCID 67200711, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To [5-(1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyrimidin-2-yl]-(5-fluoro-2-methoxy-pyridin-3-ylmethyl)-amine (125, 1 equivalent) in 15.0 mL of tetrahydrofuran, tetrabutylammonium fluoride trihydrate (2 equivalent) is added. The reaction is stirred at room temperature overnight, then poured into water and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography eluting with 20-100% ethyl acetate in hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting material is purified by silica gel column chromatography
  6. washeluting with 20-100% ethyl acetate in hexane
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-970d0ecfb0fa4a71ba0a2e877ba066d7
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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