Methyl iodide → HCID 86586785, compound

HRID 2088233Notes

Reaction equation

HRID 2088233 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([C:16]3[NH:20][N:19]=[N:18][N:17]=3)[CH2:15][C@@:9]1([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C@H:10]([O:21][C@H:22]([C:26]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=1)[CH2:23][O:24][CH3:25])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:48](=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([C:16]3[NH:17][N:18]([CH3:48])[NH:19][N:20]=3)[CH2:15][C@@:9]1([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C@H:10]([O:21][C@H:22]([C:26]1[CH:31]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:29]=[C:28]([C:36]([F:38])([F:39])[F:37])[CH:27]=1)[CH2:23][O:24][CH3:25])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178495748HCID 178495748, compound

Product 1

HCID 86586785HCID 86586785, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(1R*,2R*,5S*,6R*)-8-Benzyl-2-{(1R*)-1-[3,5-bis(trifluoromethyl)phenyl]-2-methoxyethoxy}-1-phenyl-6-(tetrazol-5-yl)-8-azabicyclo[3.2.1]octane (Example 199; 0.05 g, 0.1 mmol), methyl iodide (0.04 g 0.02 ml, 0.3 mmol) and potassium carbonate (0.04 g, 0.3 mmol) in acetonitrile were heated at 60° C. for 1.5 hours. The mixture was quenched with water and concentrated in vacuo, the residue was partitioned between water and dichloromethane using a bond elute cartridge. The organics were collected and concentrated in vacuo and the residue purified by preparative thin layer chromatography eluting with 5% methanol/dichloromethane. The title compound was isolated as a white solid (33 mg, 58%).

Workup

  1. customThe mixture was quenched with water
  2. concentrationconcentrated in vacuo
  3. customthe residue was partitioned between water and dichloromethane using a bond
  4. washelute cartridge
  5. customThe organics were collected
  6. concentrationconcentrated in vacuo
  7. customthe residue purified by preparative thin layer chromatography
  8. washeluting with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-ad18852fa8f844aebcda07bce9c7a19e
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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