HCID 59432330, compound → HCID 59432399, compound

HRID 507157Notes

Reaction equation

HRID 507157 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:20][CH2:19][CH2:18][C@H:17]([N:21]([CH2:28][C:29]3[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=3)[C:22]3[N:23]=[N:24][N:25]([CH3:27])[N:26]=3)[C:16]3[CH:43]=[C:44]([CH3:51])[C:45]([C:47]([F:50])([F:49])[F:48])=[CH:46][C:15]2=3)[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>[Pd].CO>[F:38][C:35]([F:36])([F:37])[C:33]1[CH:34]=[C:29]([CH:30]=[C:31]([C:39]([F:40])([F:41])[F:42])[CH:32]=1)[CH2:28][N:21]([C@H:17]1[CH2:18][CH2:19][CH2:20][N:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[C:15]2[CH:46]=[C:45]([C:47]([F:48])([F:49])[F:50])[C:44]([CH3:51])=[CH:43][C:16]1=2)[C:22]1[N:23]=[N:24][N:25]([CH3:27])[N:26]=1

Participants

5

Reactant 2

HCID 59432330HCID 59432330, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59432399HCID 59432399, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Subject a mixture of (S)-[1-(1-benzyl-piperidin-4-yl)-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl]-(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amine (0.130 g, 0.179 mmol) and palladium on carbon (10% by weight, wet, 0.050 g) in methanol (10 mL) to an atmosphere of hydrogen gas (35 psi) at room temperature on a Parr shaker apparatus. After 5 h, filter the mixture through celite and the concentrate the filtrate under reduced pressure. Purify the resulting residue using flash column chromatography on silica gel, eluting with hexanes/ethyl acetate (80:20), to provide the title compound as white solid (0.055 g, 48%): 1H NMR (CDCl3, 300 MHz) δ 1.63-2.13 (m, 10H), 2.34 (s, 3H), 2.82-3.0 (m, 3H), 3.10-3.22 (m, 1H), 3.33-3.41 (m, 1H), 4.09-4.13 (m, 1H), 4.14 (s, 3H), 4.74-4.97 (m, 2H), 5.12 (bs, 1H), 5.34-5.49 (m, 1H), 6.89 (s, 1H), 7.32 (s, 1H), 7.60 (s, 1H), 7.71 (s, 1H); ESI MS m/z 726 [C28H30F9N7+H]+.

Workup

  1. filtrationfilter the mixture through celite
  2. concentrationthe concentrate the filtrate under reduced pressure
  3. customPurify the resulting residue
  4. washeluting with hexanes/ethyl acetate (80:20)

Sources & evidence

ORD record
ord-3d59c22d33994eb78fade5809a68e1cb
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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