(R)-(-)-2-Amino-1-propanol → HCID 59639661, compound

HRID 556608Notes

Reaction equation

HRID 556608 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16](S(C)(=O)=O)[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[CH3:26])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:31].[NH2:32][C@H:33]([CH3:36])[CH2:34][OH:35]>C1COCC1>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]2[C:13]3[CH:12]=[CH:11][C:10](=[O:31])[N:9]([C:3]4[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=4[F:8])[C:14]=3[N:15]=[C:16]([NH:32][C@H:33]([CH3:36])[CH2:34][OH:35])[N:17]=2)=[C:20]([CH3:26])[CH:21]=1

Participants

4

Reactant 2

HCID 80308(R)-(-)-2-Amino-1-propanolHCID 596395548-(2,6-difluoro-phenyl)-4-(4-fluoro-2-methyl-phenyl)-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 59639661HCID 59639661, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 48 (200 mg, 0.45 mmol) and (R)-2-amino-1-propanol (75 mg, 1 mmol) were dissolved in THF (10 ml) and stirred under Ar at 23° for 18 h. The solvents were removed in vacuo, and the residue was partitioned between EtOAc and H2O. The organic phase was washed with H2O, satd aq NaCl, dried over anhyd Na2SO4, filtered and evaporated to give the crude product. Flash chromatography eluted with 0-15% EtOAc/CH2Cl2 gave the title compound as a off-white amorphous solid. mp 90-95°, LC MS m/z=441 (MH+) Retention time=2.09 min.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was partitioned between EtOAc and H2O
  3. washThe organic phase was washed with H2O
  4. dry with materialdried over anhyd Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude product
  8. washFlash chromatography eluted with 0-15% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-0106146612d34c5a9d1000932aea5c91
Source dataset
uspto-grants-2011_11
Patent number
US08058282B2

Reaction notes

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