Hydrochloric Acid → HCID 22674907, compound

HRID 1006366Notes

Reaction equation

HRID 1006366 reaction equation
[CH:1]([CH:14]1[CH2:19][N:18]([CH2:20][C:21]2[CH:26]=[C:25]([N:27]3[C:31]([C:32]([F:35])([F:34])[F:33])=[N:30][N:29]=[N:28]3)[CH:24]=[CH:23][C:22]=2[O:36][CH3:37])[CH2:17][CH2:16][N:15]1[CH2:38][C:39]([OH:41])=O)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:44](CC)CC)C.[I-].[Cl:50]C1C=CC=C[N+]=1C.[ClH:58]>ClCCl.N.C(OCC)(=O)C>[ClH:50].[ClH:58].[CH:1]([CH:14]1[CH2:19][N:18]([CH2:20][C:21]2[CH:26]=[C:25]([N:27]3[C:31]([C:32]([F:33])([F:35])[F:34])=[N:30][N:29]=[N:28]3)[CH:24]=[CH:23][C:22]=2[O:36][CH3:37])[CH2:17][CH2:16][N:15]1[CH2:38][C:39]([NH2:44])=[O:41])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 22674797HCID 22674797, compound

Product 1

HCID 22674907HCID 22674907, compound

Reagents, catalysts & solvents 3

HCID 222AmmoniaCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 2-[2-benzhydryl-4-[2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzyl]-1-piperazinyl]acetic acid (70 mg) and triethylamine (20 mg) in dichloromethane (5 ml) was added 2-chloro-1-methylpyridinium iodide (70 mg) at room temperature. After being stirred for 30 minutes, 28% aqueous ammonia (1 drop) was added to the solution. After being stirred for 1.5 hours, the mixture was washed with water. The organic layer was separated, dried over magnesium sulfate, and evaporated under reduced pressure. The syrup was purified by column chromatography on silica gel using a mixed solvent of dichloromethane and methanol (20:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give a syrup. The syrup was treated with 4N hydrogen chloride in ethyl acetate (1 ml) to give 2-[2-benzhydryl-4-[2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzyl]-1-piperazinyl]acetamide dihydrochloride (81 mg).

Workup

  1. stirringAfter being stirred for 1.5 hours
  2. washthe mixture was washed with water
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe syrup was purified by column chromatography on silica gel using a mixed solvent of dichloromethane and methanol (20:1)
  7. additionThe fractions containing the objective compound
  8. customwere collected
  9. customevaporated under reduced pressure
  10. customto give a syrup

Sources & evidence

ORD record
ord-235d5351588749f5824106acb8163b42
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

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