(S)-(+)-1-Aminopropan-2-ol → HCID 178462353, compound

HRID 230205Notes

Reaction equation

HRID 230205 reaction equation
Cl[C:2]1[N:3]=[C:4]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])=[N:18][NH:17][C:5]2=[N:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[F:16].[NH2:27][CH2:28][C@@H:29]([OH:31])[CH3:30]>C(O)C>[Cl:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:19]1[C:4]2[C:5](=[N:6][C:7]([O:8][C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=3[F:16])=[C:2]([NH:27][CH2:28][C@H:29]([OH:31])[CH3:30])[N:3]=2)[NH:17][N:18]=1

Participants

4

Reactant 2

HCID 7311736(S)-(+)-1-Aminopropan-2-olHCID 178505887HCID 178505887, compound

Product 1

HCID 178462353HCID 178462353, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring ethanol (100 mL) suspension of 5-Chloro-3-(2-chloro-phenyl)-6-(2,4-difluoro-phenoxy)-1H-pyrazolo[3,4-b]pyrazine (0.66 g, 1.7 mmol) under nitrogen at room temperature was added (S)-1-amino-2-propanol (0.63 g, 8.4 mmol). The reaction mixture was heated to reflux and stirred for 16 hours at reflux. The reaction mixture was cooled and concentrated under reduced pressure. The residue was chromatographed (2% MeOH in hexanes) to yield 82 mg of (R)-1-[3-(2-Chloro-phenyl)-6-(2,4-difluoro-phenoxy)-1H-pyrazolo[3,4-b]pyrazin-5-ylamino]-propan-2-ol. Mass spec., M+1=433.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperatureat reflux
  4. temperatureThe reaction mixture was cooled
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed (2% MeOH in hexanes)

Sources & evidence

ORD record
ord-ce4357289c16443384a5015beed90933
Source dataset
uspto-grants-2009_07
Patent number
US07566708B2

Reaction notes

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