HCID 59432463, compound → HCID 59432482, compound

HRID 507132Notes

Reaction equation

HRID 507132 reaction equation
C([O:8][CH2:9][CH2:10][N:11]1[CH2:17][CH2:16][CH2:15][C@H:14]([N:18]([CH2:37][C:38]2[CH:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:41]=[C:40]([C:48]([F:51])([F:50])[F:49])[CH:39]=2)[C:19]2[N:20]=[N:21][N:22]([CH2:24][CH2:25][N:26]3[C:34](=[O:35])[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:27]3=[O:36])[N:23]=2)[C:13]2[CH:52]=[C:53]([CH3:60])[C:54]([C:56]([F:59])([F:58])[F:57])=[CH:55][C:12]1=2)C1C=CC=CC=1.[H][H]>CO.[Pd]>[F:51][C:48]([F:49])([F:50])[C:40]1[CH:39]=[C:38]([CH:43]=[C:42]([C:44]([F:45])([F:46])[F:47])[CH:41]=1)[CH2:37][N:18]([C@H:14]1[CH2:15][CH2:16][CH2:17][N:11]([CH2:10][CH2:9][OH:8])[C:12]2[CH:55]=[C:54]([C:56]([F:57])([F:58])[F:59])[C:53]([CH3:60])=[CH:52][C:13]1=2)[C:19]1[N:20]=[N:21][N:22]([CH2:24][CH2:25][N:26]2[C:27](=[O:36])[C:28]3[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:34]2=[O:35])[N:23]=1

Participants

5

Reactant 2

HCID 59432463HCID 59432463, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59432482HCID 59432482, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-2-(2-{5-[[1-(2-Benzyloxy-ethyl)-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl]-(3,5-bis-trifluoromethyl-benzyl)-amino]-tetrazol-2-yl}-ethyl)-isoindole-1,3-dione (Example 126, Step 3) (0.09 mmol) in methanol (20 mL), add a catalytic amount of 10% Pd/C after purging with nitrogen. Purge the reaction with a balloon of hydrogen and stir under a balloon of hydrogen for 14 h. Purge the reaction with nitrogen and filter through Celite®. Collect the filtrate and remove solvent under vacuum. Chromatograph the reaction over silica gel eluting with ethyl acetate/hexane (15-45%) to afford the title compound.

Workup

  1. customafter purging with nitrogen
  2. customPurge
  3. customthe reaction with a balloon of hydrogen
  4. customPurge
  5. customthe reaction with nitrogen
  6. filtrationfilter through Celite®
  7. customCollect the filtrate
  8. customremove solvent under vacuum
  9. customChromatograph the reaction over silica gel eluting with ethyl acetate/hexane (15-45%)

Sources & evidence

ORD record
ord-5ae16ce0b22f42599494a64448f40bf8
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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