Water → HCID 58485842, compound

HRID 1396176Notes

Reaction equation

HRID 1396176 reaction equation
C1(S([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([CH:19]4[CH2:21][CH2:20]4)[C:13]=3[C:12]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([NH:30][C:31]4[CH:32]=[N:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=4)=[N:27][C:28]=3[F:29])=[CH:11]2)(=O)=O)C=CC=CC=1.O>O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:19]1([C:18]2[C:13]3[C:12]([CH2:22][C:23]4[CH:24]=[CH:25][C:26]([NH:30][C:31]5[CH:32]=[N:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=5)=[N:27][C:28]=4[F:29])=[CH:11][NH:10][C:14]=3[N:15]=[CH:16][N:17]=2)[CH2:20][CH2:21]1

Participants

5

Reactant 2

HCID 962WaterHCID 58485691HCID 58485691, compound

Product 1

HCID 58485842HCID 58485842, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

To [5-(7-benzenesulfonyl-4-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-6-fluoro-pyridin-2-yl]-(6-methoxy-pyridin-3-yl)-amine (76, 0.170 g, 0.320 mmol) in 10.0 mL of tetrahydrofuran, tetrabutylammonium fluoride, trihydrate (0.174 g, 0.551 mmol) is added and the reaction is stirred at room temperature overnight. The reaction is poured into water and extracted with ethyl acetate. The organic layer is dried with 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 (P-4023, 100.4 mg). MS (ESI) [M+H+]+=390.8.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried with 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-021a33e4c071408cbe7778eb795686f2
Source dataset
uspto-grants-2014_12
Patent number
US08901118B2

Reaction notes

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