Acetic Anhydride → N-[3-(4-{6-[3-(4-Fluorophenyl)-1-trityl-1H-4-pyrazolyl]-imidazo[1,2-a]pyridin-3-yl}phenoxy)propyl]acetamide

HRID 1792515Notes

Reaction equation

HRID 1792515 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([C:19]([C:22]5[CH:32]=[CH:31][C:25]([O:26][CH2:27][CH2:28][CH2:29][NH2:30])=[CH:24][CH:23]=5)=[CH:20][N:21]=4)[CH:18]=3)=[CH:11][N:10]([C:33]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:59](OC(=O)C)(=[O:61])[CH3:60].C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([C:19]([C:22]5[CH:32]=[CH:31][C:25]([O:26][CH2:27][CH2:28][CH2:29][NH:30][C:59](=[O:61])[CH3:60])=[CH:24][CH:23]=5)=[CH:20][N:21]=4)[CH:18]=3)=[CH:11][N:10]([C:33]([C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 220310713-(4-{6-[3-(4-Fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}phenoxy)propylamine

Product 1

HCID 22032216N-[3-(4-{6-[3-(4-Fluorophenyl)-1-trityl-1H-4-pyrazolyl]-imidazo[1,2-a]pyridin-3-yl}phenoxy)propyl]acetamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

While 5 mL solution of 37 mg 3-(4-{6-[3-(4-Fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}phenoxy)-propylamine obtained in Example 16 and 20 mg triethylamine in dichloromethane was stirred under ice-coolingd water in a stream of nitrogen, 9 μL acetic anhydride was added thereto and stirred for 1 hour. An aqueous saturated sodium bicarbonate solution and ethyl acetate were added to the reaction solution, the organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The drying agent was filtered off, the filtrate was concentrated, and the residue was purified by NH silica gel column chromatography (hexane/ethyl acetate) to give 30 mg of the title compound as a colorless oil.

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe drying agent was filtered off
  6. concentrationthe filtrate was concentrated
  7. customthe residue was purified by NH silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1d936ddfd3c54eee965be322edd313ac
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

Loading…