Water → HCID 24952873, compound

HRID 1024270Notes

Reaction equation

HRID 1024270 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]=[CH:24][C:25]([NH:29][CH2:30][C:31]4[CH:32]=[N:33][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:35][CH:36]=4)=[N:26][C:27]=3[F:28])=[CH:11]2)(=O)=O)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[F:28][C:27]1[N:26]=[C:25]([NH:29][CH2:30][C:31]2[CH:32]=[N:33][C:34]([C:37]([F:40])([F:38])[F:39])=[CH:35][CH:36]=2)[CH:24]=[CH:23][C:22]=1[CH2:21][C:12]1[C:13]2[C:14](=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=2)[NH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 57619272HCID 57619272, compound

Product 1

HCID 24952873HCID 24952873, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To [5-(1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-yl]-(6-trifluoromethyl-pyridin-3-ylmethyl)-amine (577, 0.08 g, 0.13 mmol) in tetrahydrofuran (10.0 mL) was added tetrabutylammonium fluoride, trihydrate (0.110 g, 0.35 mmol). The reaction was stirred at room temperature overnight, then poured into water, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% to 100% ethyl acetate in hexane to give an off-white solid (P-0187, 8.1 mg, 10%). MS (ESI) [M+H+]+=431.9.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 20% to 100% ethyl acetate in hexane
  7. customto give an off-white solid (P-0187, 8.1 mg, 10%)

Sources & evidence

ORD record
ord-8760b19441fc4a16a14ec8e75007ef58
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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