Water → 3-(4-{6-[3-(4-Fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}phenoxy)propylamine

HRID 1792514Notes

Reaction equation

HRID 1792514 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:34]=[CH:33][C:25]([O:26][CH2:27][CH2:28][CH2:29][N:30]=[N+]=[N-])=[CH:24][CH:23]=5)=[CH:20][N:21]=4)[CH:18]=3)=[CH:11][N:10]([C:35]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:9]=2)=[CH:4][CH:3]=1.C(P)CCC.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.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:34]=[CH:33][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:35]([C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 2784062ButylphosphineHCID 220318643-(4-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}phenoxy)-propyl azide

Product 1

HCID 220310713-(4-{6-[3-(4-Fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}phenoxy)propylamineYield 84.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 351 mg 3-(4-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}phenoxy)-propyl azide obtained in Example 15 in 10 mL tetrahydrofuran was stirred at room temperature in a stream of nitrogen, 0.15 mL n-butyl phosphine was added thereto and stirred for 2 hours. Then, 2 mL water was added thereto and further stirred for 4 hours. Ethyl acetate and anhydrous sodium sulfate were added to the reaction solution and stirred. The drying agent was filtered off, the filtrate was concentrated, and the residue was subjected to silica gel column chromatography. By gradual elution with an eluent from hexane:ethyl acetate=1:1 (v/v) to ethyl acetate:methanol 100:1 (v/v), 287 mg of the title compound was obtained as a pale brown amorphous.

Workup

  1. additionwas added
  2. stirringfurther stirred for 4 hours
  3. stirringstirred
  4. filtrationThe drying agent was filtered off
  5. concentrationthe filtrate was concentrated
  6. washBy gradual elution with an eluent from hexane

Sources & evidence

ORD record
ord-80dfa5754aae434986bc35ed32398ad0
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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