Sodium hydride → HCID 67127407, compound

HRID 1520710Notes

Reaction equation

HRID 1520710 reaction equation
[F:1][C:2]1([CH2:12][OH:13])[CH2:7][CH2:6][N:5]([CH:8]2[CH2:11][O:10][CH2:9]2)[CH2:4][CH2:3]1.[H-].[Na+].[C:16]([C:18]1[CH:19]=[C:20]([S:25]([NH2:28])(=[O:27])=[O:26])[CH:21]=[CH:22][C:23]=1F)#[N:17]>O1CCCC1>[C:16]([C:18]1[CH:19]=[C:20]([S:25]([NH2:28])(=[O:27])=[O:26])[CH:21]=[CH:22][C:23]=1[O:13][CH2:12][C:2]1([F:1])[CH2:3][CH2:4][N:5]([CH:8]2[CH2:9][O:10][CH2:11]2)[CH2:6][CH2:7]1)#[N:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 251398973-Cyano-4-fluorobenzene-1-sulfonamideHCID 67126802HCID 67126802, compound

Product 1

HCID 67127407HCID 67127407, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 517B (0.185 g) in tetrahydrofuran (5 mL) was added sodium hydride (0.090 g). After 30 minutes, 3-cyano-4-fluorobenzenesulfonamide (0.178 g) was added in one portion. The reaction was stirred at room temperature for 2 hours. The reaction was quenched with 1N aqueous HCl (4 mL), diluted with dichloromethane (30 mL) and saturated aqueous NaHCO3 (25 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated. The resulting solid material was triturated with dichloromethane and filtered to give the title compound.

Workup

  1. customThe reaction was quenched with 1N aqueous HCl (4 mL)
  2. additiondiluted with dichloromethane (30 mL) and saturated aqueous NaHCO3 (25 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting solid material was triturated with dichloromethane
  7. filtrationfiltered

Sources & evidence

ORD record
ord-ac17b0b30d5f40c9a288199d2bbef391
Source dataset
uspto-grants-2015_07
Patent number
US09073855B2

Reaction notes

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