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

HRID 2168033Notes

Reaction equation

HRID 2168033 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-900ee29fe0d6433388bd3309cb44e5e6
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

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