Hydrochloric Acid → 4-(1-Allyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(4-fluorophenyl)-3-[2-(1(S)-phenylethylamino)pyridin-4-yl]-1H-pyrrole

HRID 1245016Notes

Reaction equation

HRID 1245016 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH:11]=[C:10]([C:13]2[C:14]([C:25]3[CH:30]=[CH:29][N:28]=[C:27](F)[CH:26]=3)=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[NH:16][CH:17]=2)[CH2:9][CH2:8]1)=[O:6])[CH:2]=[CH2:3].[C:32]1([C@@H:38]([NH2:40])[CH3:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.Cl.C(=O)([O-])O.[Na+]>>[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH:11]=[C:10]([C:13]2[C:14]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:40][C@H:38]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH3:39])[CH:26]=3)=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[NH:16][CH:17]=2)[CH2:9][CH2:8]1)=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 758181-Phenethylamine, (-)-HCID 516892Sodium BicarbonateHCID 219226854-(1-Allyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl]-2-(4-fluorophenyl)-3-(2-fluoropyridin-4-yl)-1H-pyrrole

Product 1

HCID 575018174-(1-Allyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(4-fluorophenyl)-3-[2-(1(S)-phenylethylamino)pyridin-4-yl]-1H-pyrroleYield 51.6%

Conditions

Temperature
150 °C

Procedure

A mixture of 360 mg (0.85 mmol) of 4-(1-allyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(4-fluorophenyl)-3-(2-fluoropyridin-4-yl)-1H-pyrrole [prepared as described in step 73 (ii) above], 3.6 ml (28.3 mmol) of 1(S)-phenylethylamine and 0.36 ml of concentrated hydrochloric acid was stirred at 150° C. for 10 hours. At the end of this time, a saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture and then this was extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure. The residue thus obtained was purified by chromatography on a silica gel column using a 1:1 by volume mixture of hexane and ethyl acetate as the eluant to give 229 mg (yield 49%) of the title compound as a brown amorphous solid.

Workup

  1. extractionthis was extracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by chromatography on a silica gel column
  8. additionby volume mixture of hexane and ethyl acetate as the eluant

Sources & evidence

ORD record
ord-e39f7322e45c418fa1b28f9a5c7cea9c
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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