HCID 67981041, compound → HCID 68048119, compound

HRID 1408869Notes

Reaction equation

HRID 1408869 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]23[CH2:18][C:15]([NH:19]C(=O)OCC4C=CC=CC=4)([CH2:16][CH2:17]2)[CH2:14][CH2:13][CH2:12]3)=[O:10])[CH:5]=[CH:4][N:3]=1>Br.CC(O)=O>[NH2:19][C:15]12[CH2:18][C:11]([C:9]([NH:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[N:7]=3)=[O:10])([CH2:17][CH2:16]1)[CH2:12][CH2:13][CH2:14]2

Participants

3

Reactant 1

HCID 67981041HCID 67981041, compound

Product 1

HCID 68048119HCID 68048119, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

A solution of benzyl 5-(2-methylpyrimidin-4-ylcarbamoyl)bicyclo[3.2.1]octan-1-ylcarbamate (1 g, 2.5 mmol) in HBr/HOAc (33% solution, 8 mL) was stirred at room temperature for an hour and then concentrated under reduced pressure. The resulting residue was dissolved in aq. HCl (6N, 10 mL) and extracted with ethyl acetate (10 mL) to remove the organic impurities. The aqueous phase was basified with aq. NaOH (6N, 4 mL), and then extracted with DCM (4×20 mL). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford 350 mg (66%) of 5-amino-N-(2-methylpyrimidin-4-yl)bicyclo[3.2.1]octane-1-carboxamide as a white solid ESI-MS m/z: 261 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in aq. HCl (6N, 10 mL)
  3. extractionextracted with ethyl acetate (10 mL)
  4. customto remove the organic impurities
  5. extractionextracted with DCM (4×20 mL)
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7602d63dec5547feb9b864df9dfd426c
Source dataset
uspto-grants-2014_12
Patent number
US08921370B2

Reaction notes

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