Hydrochloric Acid → HCID 57418746, compound

HRID 909154Notes

Reaction equation

HRID 909154 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11][C:12]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:13]=3[C:14]#[N:15])=[CH:8][CH:9]=2)[CH:4]=[N:3]1.Cl>CO.[OH-].[OH-].[Pd+2]>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([S:11][C:12]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:13]=3[CH2:14][NH2:15])=[CH:8][CH:9]=2)[CH:4]=[N:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57418745HCID 57418745, compound

Product 1

HCID 57418746HCID 57418746, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of compound (4r), (0.43 g, 1.5 mmol) in MeOH (30 mL) was purged with nitrogen and treated with Pd(OH)2/C catalyst (15% wt, 280 mg, 0.3 mmol) followed by concentrated HCl (0.38 mL, 4.6 mmol). After purging more with nitrogen, a hydrogen-filled balloon was placed on top of the flask. After stirring at room temperature for 18 hours, the LC showed no more starting material. Next, K2CO3 (0.5 g) was added. The catalyst was filtered through a plug of silicagel/celite/sand and washed with CHCl3/Et3N and the solvent was removed under reduced pressure. The resulting pale yellow foam (5r), (0.43 g, 87% isolated yield) was stored under a nitrogen atmosphere. MS (ESI) m/z 287.9 (M+H)+.

Workup

  1. customAfter purging more with nitrogen
  2. additiona hydrogen-filled balloon
  3. additionNext, K2CO3 (0.5 g) was added
  4. filtrationThe catalyst was filtered through a plug of silicagel/celite/sand
  5. washwashed with CHCl3/Et3N
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-dca31e2d38134898ad722139ffd11de8
Source dataset
uspto-grants-2011_09
Patent number
US08017641B2

Reaction notes

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