HCID 178423619, compound → HCID 178423621, compound

HRID 2068519Notes

Reaction equation

HRID 2068519 reaction equation
[F:1][C:2]([F:45])([F:44])[C:3]1[CH:4]=[C:5]([CH2:13][N:14]([C:38]2[N:39]=[N:40][N:41]([CH3:43])[N:42]=2)[C@@H:15]2[C:21]3[CH:22]=[C:23]([CH3:27])[CH:24]=[C:25]([CH3:26])[C:20]=3[N:19]([CH2:28][C@H:29]3[CH2:34][CH2:33][C@H:32]([C:35]([OH:37])=[O:36])[CH2:31][CH2:30]3)[CH2:18][CH2:17][CH2:16]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1>O>[OH2:36].[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([CH2:13][N:14]([C:38]2[N:39]=[N:40][N:41]([CH3:43])[N:42]=2)[C@@H:15]2[C:21]3[CH:22]=[C:23]([CH3:27])[CH:24]=[C:25]([CH3:26])[C:20]=3[N:19]([CH2:28][C@H:29]3[CH2:34][CH2:33][C@H:32]([C:35]([OH:37])=[O:36])[CH2:31][CH2:30]3)[CH2:18][CH2:17][CH2:16]2)[CH:4]=[C:3]([C:2]([F:1])([F:45])[F:44])[CH:8]=1

Participants

3

Reactant 1

HCID 178423619HCID 178423619, compound

Product 1

HCID 178423621HCID 178423621, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Charge a flask with Trans-4-[[(5S)-5-[[[3,5-bis(trifluoromethyl)phenyl]methyl](2-methyl-2H-tetrazol-5-yl)amino]-2,3,4,5-tetrahydro-7,9-dimethyl-1H-1-benzazepin-1-yl]methyl]-cyclohexanecarboxylic acid (15.87 kg) and water (158.8 L). Stir the resulting mixture at RT for 2 hrs. Thereafter filter the resulting mixture to collect the solids. Dry the solids over night. The resulting solids were dissolved in MeOH heated to about 65-70° C. for 2 hrs to provide a clear solution. Filter the clear solution, then cool the filtrate to about 0 to 5° C. to induce crystallization. Collect the resulting crystals, and dry overnight. Suspend the crystalline material in water (158.8 L) and stir for about 2 hrs at RT. Collect the crystalline solid; dry at high vacuum at 40-45° C. to provide a solid that exhibits a water content of between 2.7 to 3.1 as determined by the Karl Fischer method.

Workup

  1. filtrationThereafter filter the resulting mixture
  2. customto collect the solids
  3. customDry the solids over night
  4. dissolutionThe resulting solids were dissolved in MeOH
  5. temperatureheated to about 65-70° C. for 2 hrs
  6. customto provide a clear solution
  7. filtrationFilter the clear solution
  8. temperaturecool the filtrate to about 0 to 5° C.
  9. customcrystallization
  10. customCollect the resulting crystals
  11. customdry overnight
  12. stirringstir for about 2 hrs at RT
  13. customCollect the crystalline solid
  14. customdry at high vacuum at 40-45° C.
  15. customto provide a solid that exhibits a water content of between 2.7 to 3.1

Sources & evidence

ORD record
ord-6e6971fb502d4138a26d836b2f950871
Source dataset
uspto-grants-2012_10
Patent number
US08299060B2

Reaction notes

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