Water → (Rac)-3-(3-(4-(benzo[d]thiazol-2-ylamino)-3-fluorophenoxy)pyrazin-2-yl)cyclohex-2-enol

HRID 887413Notes

Reaction equation

HRID 887413 reaction equation
[BH4-].[Na+].[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C:13]1[CH:32]=[CH:31][C:16]([O:17][C:18]2[C:19]([C:24]3[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[CH:25]=3)=[N:20][CH:21]=[CH:22][N:23]=2)=[CH:15][C:14]=1[F:33].[Cl-].[NH4+].O>CO>[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C:13]1[CH:32]=[CH:31][C:16]([O:17][C:18]2[C:19]([C:24]3[CH2:29][CH2:28][CH2:27][CH:26]([OH:30])[CH:25]=3)=[N:20][CH:21]=[CH:22][N:23]=2)=[CH:15][C:14]=1[F:33]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 593513153-(3-(4-(Benzo[d]thiazol-2-ylamino)-3-fluorophenoxy)pyrazin-2-yl)cyclohex-2-enone

Product 1

HCID 59351328(Rac)-3-(3-(4-(benzo[d]thiazol-2-ylamino)-3-fluorophenoxy)pyrazin-2-yl)cyclohex-2-enol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium tetrahydroborate (157 mg, 4.16 mmol) was added to a suspension of 3-(3-(4-(benzo[d]thiazol-2-ylamino)-3-fluorophenoxy)pyrazin-2-yl)cyclohex-2-enone (600 mg, 1.387 mmol) in MeOH (20 ml) at RT. The mixture was stirred at RT for 1 h, and was then cooled in an ice-water bath. Saturated aqueous ammonium chloride (5 ml) was added along with distilled water (100 ml). The resulting mixture was extracted with EtOAc (2×100 ml), and the combined organic layers were washed with brine and dried over sodium sulfate. Filtration and concentration under reduced pressure, followed by flash chromatography on silica gel (30% to 60% EtOAc in hexanes) afforded (rac)-3-(3-(4-(benzo[d]thiazol-2-ylamino)-3-fluorophenoxy)pyrazin-2-yl)cyclohex-2-enol as a white solid. MS (ESI, pos. ion) m/z: 435.0 (M+1). IC50 (uM) +++++.

Workup

  1. temperaturewas then cooled in an ice-water bath
  2. extractionThe resulting mixture was extracted with EtOAc (2×100 ml)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-ed13d809f5134e71892bb69139a94e6e
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

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