Triethylamine → 2-[(3S)-3-Amino-1-pyrrolidinyl]-N-(cyclohexylmethyl)-5-quinolinecarboxamide

HRID 2217850Notes

Reaction equation

HRID 2217850 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:16]=[CH:15][C:14]3[C:13]([C:17]([NH:19][CH2:20][CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[O:18])=[C:12](Cl)[CH:11]=[CH:10][C:9]=3[N:8]=2)[CH2:3]1.C(N(CC)CC)C.[H][H]>C(O)C.[Pd]>[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:16]=[CH:15][C:14]3[C:13]([C:17]([NH:19][CH2:20][CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[O:18])=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=2)[CH2:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 111766692-[(3S)-3-Amino-1-pyrrolidinyl]-6-chloro-N-(cyclohexylmethyl)-5-quinolinecarboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 597686202-[(3S)-3-Amino-1-pyrrolidinyl]-N-(cyclohexylmethyl)-5-quinolinecarboxamideYield 54.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2-[(5)-3-amino-1-pyrrolidinyl]-6-chloro-N-(cyclohexylmethyl)-5-quinolinecarboxamide (Example 44) (0.10 g) and triethylamine (0.04 mL) in ethanol (20 mL) was treated with 5% palladium on charcoal (0.05 g) and stirred under 2 atmospheres of hydrogen at ambient temperature for 16 hours. The reaction mixture was filtered through Celite and the liquors concentrated to dryness. Recrystallisation from methanol/ethyl acetate afforded to title compound (0.05 g).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe liquors concentrated to dryness
  3. customRecrystallisation from methanol/ethyl acetate

Sources & evidence

ORD record
ord-1e3c83ef95674670a963ca4b506939f5
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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