Pyridine → HCID 11585433, compound

HRID 507134Notes

Reaction equation

HRID 507134 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[CH2:6][N:7]([C:27]1[N:28]=[N:29][N:30]([CH3:32])[N:31]=1)[C@H:8]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][CH2:16][OH:17])[C:10]2[CH:18]=[C:19]([C:23]([F:26])([F:25])[F:24])[C:20]([CH3:22])=[CH:21][C:9]1=2.N1C=CC=CC=1.[C:48](Cl)(=[O:50])[CH3:49]>ClCCl>[F:37][C:36]([F:39])([F:38])[C:34]1[CH:33]=[C:5]([CH:4]=[C:3]([C:2]([F:40])([F:1])[F:41])[CH:35]=1)[CH2:6][N:7]([C:27]1[N:28]=[N:29][N:30]([CH3:32])[N:31]=1)[C@H:8]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][CH2:16][O:17][C:48](=[O:50])[CH3:49])[C:10]2[CH:18]=[C:19]([C:23]([F:24])([F:25])[F:26])[C:20]([CH3:22])=[CH:21][C:9]1=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 11548876HCID 11548876, compound

Product 1

HCID 11585433HCID 11585433, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-2-{5-[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl}-ethanol (Example 130, Step 2) (0.12 mmol) in dichloromethane (5 mL), add pyridine (0.47 mmol) followed by acetyl chloride (0.47 mmol). After stirring at room temperature for 14 h, quench the reaction with water (5 mL) and dilute with dichloromethane (5 mL). Separate the organic phase and wash the aqueous with dichloromethane (2×5 mL). Dry the combined organics over sodium sulfate, filter, and remove solvent under vacuum. Chromatograph the product over silica gel, eluting with ethyl acetate/hexane (5-40%), to afford the title compound as a colorless foam. MS (ES+): 639 (M+H).

Workup

  1. customquench
  2. customthe reaction with water (5 mL)
  3. customSeparate the organic phase
  4. washwash the aqueous with dichloromethane (2×5 mL)
  5. dry with materialDry the combined organics over sodium sulfate
  6. filtrationfilter
  7. customremove solvent under vacuum
  8. washChromatograph the product over silica gel, eluting with ethyl acetate/hexane (5-40%)

Sources & evidence

ORD record
ord-295ade288c2644ddba974b1678d54514
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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