Dimethylformamide → 4-((1-(1,3-Difluoropropan-2-yl)-4-fluoropiperidin-4-yl)methoxy)-3-nitrobenzenesulfonamide

HRID 573164

Reaction equation

HRID 573164 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.[F:23][CH2:24][C:25](=O)[CH2:26][F:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CN(C)C=O>ClCCl>[F:23][CH2:24][CH:25]([N:5]1[CH2:6][CH2:7][C:2]([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])([F:1])[CH2:3][CH2:4]1)[CH2:26][F:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 2283971,3-Difluoroacetone2×HCID 5049666Sodium triacetoxyborohydride2×HCID 671265024((4-Fluoropiperidin-4-yl)methoxy)-3-nitrobenzenesulfonamide

Product 1

HCID 674229314-((1-(1,3-Difluoropropan-2-yl)-4-fluoropiperidin-4-yl)methoxy)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of EXAMPLE 341C (0.100 g) and 1,3-difluoropropan-2-one (0.025 g) in dichloromethane (2 mL) was added sodium triacetoxyborohydride (0.071 g). After 15 minutes, N,N-dimethylformamide was added dropwise until an orange solution resulted (−15 drops). After stirring overnight additional 1,3-difluoropropan-2-one and sodium triacetoxyborohydride were added. After 3 hours, the reaction was loaded onto silica gel (Reveleris 40 g) and eluted with a gradient of 0.5-5% methanol/dichloromethane over 30 minutes (flow=40 ml/minutes) to provide the title compound.

Workup

  1. customresulted (−15 drops)
  2. additionwere added
  3. waitAfter 3 hours
  4. washeluted with a gradient of 0.5-5% methanol/dichloromethane over 30 minutes (flow=40 ml/minutes)

Sources & evidence

ORD record
ord-16aaffaa1c0345aea03d2c6139ed2bc1
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Linked notes

Loading…