2-Amino-2-methyl-1-propanol → HCID 59639589, compound

HRID 2249805Notes

Reaction equation

HRID 2249805 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:21]=[CH:20][C:19](=[O:22])[N:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[F:29])[C:10]=3[N:11]=[C:12](S(C)(=O)=O)[N:13]=2)=[C:4]([CH3:30])[CH:3]=1.[NH2:31][C:32]([CH3:36])([CH3:35])[CH2:33][OH:34]>C1COCC1>[CH3:35][C:32]([NH:31][C:12]1[N:13]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[CH3:30])[C:9]2[CH:21]=[CH:20][C:19](=[O:22])[N:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[C:10]=2[N:11]=1)([CH3:36])[CH2:33][OH:34]

Participants

4

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 10113314HCID 10113314, compound

Product 1

HCID 59639589HCID 59639589, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 59 (200 mg, 0.47 mmol) and 2-amino-2-methyl-1-propanol (94 mg, 1 mmol) were dissolved in THF (10 ml) and stirred under Ar at 50° for 3 days. 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 light-yellow amorphous solid. mp 106-112°, LC MS m/z=437 (MH+) Retention time=1.94 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-4af9a996e41747f98656beb41a5e936f
Source dataset
uspto-grants-2008_01
Patent number
US07314881B2

Reaction notes

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