Acetic Acid → 4-((4-Fluoro-1-(tetrahydro-2h-pyran-4-yl)piperidin-4-yl)methoxy)-3-nitrobenzenesulfonamide

HRID 574849

Reaction equation

HRID 574849 reaction equation
[F:1][C:2]1([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:12][C:11]=2[N+:20]([O-:22])=[O:21])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[O:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1.C([BH3-])#N.[Na+].C(O)(=O)C>O1CCCC1>[F:1][C:2]1([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:12][C:11]=2[N+:20]([O-:22])=[O:21])[CH2:7][CH2:6][N:5]([CH:26]2[CH2:27][CH2:28][O:23][CH2:24][CH2:25]2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5003444Sodium cyanoborohydrideHCID 671265024((4-Fluoropiperidin-4-yl)methoxy)-3-nitrobenzenesulfonamide

Product 1

HCID 671265484-((4-Fluoro-1-(tetrahydro-2h-pyran-4-yl)piperidin-4-yl)methoxy)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of EXAMPLE 173A (0.4 g), dihydro-2H-pyran-4(3H)-one (0.179 g), sodium cyanoborohydride (0.112 g), and acetic acid (0.5 mL) in tetrahydrofuran (3 mL) was stirred overnight. The solvents were removed under reduced pressure. The residue was purified with flash column chromatography on silica gel eluting with 100:5:0.5 ethyl acetate/methanol/NH4OH to give the desired product.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customThe residue was purified with flash column chromatography on silica gel eluting with 100:5:0.5 ethyl acetate/methanol/NH4OH

Sources & evidence

ORD record
ord-f051abd3670b4cfd8491b8337eb7c63c
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Linked notes

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