HCID 89963153, compound → HCID 89962247, compound

HRID 337996Notes

Reaction equation

HRID 337996 reaction equation
[Cl:1][C:2]1[C:3]([O:19][C@H:20]2[CH2:25][CH2:24][CH2:23][CH2:22][C@@H:21]2[C:26]2[N:30](COCCOC)[N:29]=[CH:28][CH:27]=2)=[CH:4][C:5]([F:18])=[C:6]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:7]=1>Cl.CO>[Cl:1][C:2]1[C:3]([O:19][C@H:20]2[CH2:25][CH2:24][CH2:23][CH2:22][C@@H:21]2[C:26]2[NH:30][N:29]=[CH:28][CH:27]=2)=[CH:4][C:5]([F:18])=[C:6]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:7]=1

Participants

4

Reactant 1

HCID 89963153HCID 89963153, compound

Product 1

HCID 89962247HCID 89962247, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of the 5-chloro-2-fluoro-4-{[(1S,2R)-2-{1-[(2-methoxyethoxy)methyl]-1H-pyrazol-5-yl}cyclohexyl]oxy}-N-(pyrimidin-4-yl)benzenesulfonamide (120 mg, 0.222 mmol) prepared in Example 158d in 6 M HCl (5.0 mL) and methanol (4.0 mL) was stirred for 5 hours under heated reflux. The reaction solution was concentrated, and the residue was purified with silica gel chromatography (dichloromethane/methanol=85:15) to yield the title compound (80.0 mg, 80%) as a pale yellow solid.

Workup

  1. temperatureunder heated
  2. temperaturereflux
  3. concentrationThe reaction solution was concentrated
  4. customthe residue was purified with silica gel chromatography (dichloromethane/methanol=85:15)

Sources & evidence

ORD record
ord-a7284dc74522472c8c56c41eb64eaeee
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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