Acetone → HCID 178485824, compound

HRID 333498Notes

Reaction equation

HRID 333498 reaction equation
CC(C)=[O:3].[ClH:5].Cl.[CH3:7][O:8][C:9](=[O:65])[NH:10][C@H:11]([C:15]([N:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[C:22]1[NH:23][CH:24]=[C:25]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36]([NH:39][C:40]([C:42]4[CH:43]=[N:44][C:45]([N:48]5[CH2:53][C@H:52]([CH3:54])[N:51]([C:55](=[O:58])[NH:56][CH3:57])[CH2:50][C@H:49]5[CH3:59])=[CH:46][CH:47]=4)=[O:41])=[CH:35][C:34]=3[O:60][C:61]([F:64])([F:63])[F:62])=[CH:29][CH:28]=2)[N:26]=1)=[O:16])[CH:12]([CH3:14])[CH3:13]>C(O)C>[OH2:3].[ClH:5].[ClH:5].[CH3:7][O:8][C:9](=[O:65])[NH:10][C@H:11]([C:15]([N:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[C:22]1[NH:23][CH:24]=[C:25]([C:27]2[CH:28]=[CH:29][C:30]([C:33]3[CH:38]=[CH:37][C:36]([NH:39][C:40]([C:42]4[CH:43]=[N:44][C:45]([N:48]5[CH2:53][C@H:52]([CH3:54])[N:51]([C:55](=[O:58])[NH:56][CH3:57])[CH2:50][C@H:49]5[CH3:59])=[CH:46][CH:47]=4)=[O:41])=[CH:35][C:34]=3[O:60][C:61]([F:64])([F:62])[F:63])=[CH:31][CH:32]=2)[N:26]=1)=[O:16])[CH:12]([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 180AcetoneHCID 178485823HCID 178485823, compound

Product 1

HCID 178485824HCID 178485824, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

Ethanol (2 mL) and acetone (15 mL) were added to amorphous ((S)-1-{(S)-2-[4-(4′-{[6-((2R,5S)-2,5-dimethyl-4-methylcarbamoyl-piperazin-1-yl)-pyridine-3-carbonyl]-amino}-2′-trifluoromethoxy-biphenyl-4-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester diHCl (1102 mg, Example 4). The reaction mixture was warmed to 60° C. and sonicated for 1 min to give a hazy solution. Ethanol (2 mL) was added to provide a clear solution, which was heated at 60° C. After about 5 mL of solvent had evaporated, acetone (10 mL) was added until the solution turned cloudy. The contents were stirred overnight to provide a crystalline slurry which was stirred for an additional 48 h and then allowed to settle. The supernatant solvents were decanted. To the remaining solid suspension was added water (0.5 mL) and dioxane (2 mL). The resulting mixture was filtered to give a white to off-white solid which was dried under vacuum for 12 h to provide the title compound (628 mg).

Workup

  1. customsonicated for 1 min
  2. customto give a hazy solution
  3. customto provide a clear solution, which
  4. temperaturewas heated at 60° C
  5. customAfter about 5 mL of solvent had evaporated
  6. additionacetone (10 mL) was added until the solution
  7. customto provide a crystalline slurry which
  8. stirringwas stirred for an additional 48 h
  9. customThe supernatant solvents were decanted
  10. additionTo the remaining solid suspension was added water (0.5 mL) and dioxane (2 mL)
  11. filtrationThe resulting mixture was filtered
  12. customto give a white to off-white solid which
  13. customwas dried under vacuum for 12 h

Sources & evidence

ORD record
ord-e52b82f608ef40f68c9e15e36c0d83df
Source dataset
uspto-grants-2014_11
Patent number
US08883135B2

Reaction notes

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