Sodium hydride → HCID 57527174, compound

HRID 1452984Notes

Reaction equation

HRID 1452984 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:13]([C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])=[O:17])[C:14]#[N:15])=[N:6][C:7]=1[S:8]([CH2:11]C)(=O)=O.[H-].[Na+]>CN(C=O)C>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:16](=[O:17])[CH:13]([C:5]1[N:6]=[C:7]2[S:8][C:11]([NH:1][CH:2]([CH3:3])[CH3:7])=[N:1][C:2]2=[CH:3][CH:4]=1)[C:14]#[N:15]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 67343379HCID 67343379, compound

Product 1

HCID 57527174HCID 57527174, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(5-amino-6-(ethylsulfonyl)pyridin-2-yl)-3-(2-fluorophenyl)-3-oxopropanenitrile (presumed 0.951 mmol, 1.0 eq.) and iPrNCS (0.15 mL, 1.43 mmol, 1.5 eq.) in DMF (4.8 mL) under nitrogen at 0° C. was added NaH (95%; 0.0982 g, 3.89 mmol, 4.1 eq.). After 0.75 hr, the cold bath was removed and the reaction was stirred to room temperature for 0.5 hr. At 0° C., iPrNCS (0.1 mL) and NaH (0.050 g) were added and stirred for 0.25 hr. The cold bath was removed, and the reaction was stirred to room temperature overnight. At 0° C., water and EtOAc were added, and separated. The aqueous layer was washed with EtOAc (2×). The aqueous layer was concentrated in vacuo. Silica gel chromatography using CH2Cl2:MeOH (100:1) as eluent afforded 3-(2-fluorophenyl)-2-(2-(isopropylamino)thiazolo[5,4-b]pyridin-5-yl)-3-oxopropanenitrile as a burgundy solid (0.10 g, 29%).

Workup

  1. customthe cold bath was removed
  2. additionAt 0° C., iPrNCS (0.1 mL) and NaH (0.050 g) were added
  3. stirringstirred for 0.25 hr
  4. customThe cold bath was removed
  5. stirringthe reaction was stirred to room temperature overnight
  6. additionAt 0° C., water and EtOAc were added
  7. customseparated
  8. washThe aqueous layer was washed with EtOAc (2×)
  9. concentrationThe aqueous layer was concentrated in vacuo

Sources & evidence

ORD record
ord-96a18e4e62b04e00bc958134771c23fd
Source dataset
uspto-grants-2009_01
Patent number
US07473784B2

Reaction notes

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