(S)-(-)-2-Aminomethyl-1-ethylpyrrolidine → HCID 178472022, compound

HRID 1047161Notes

Reaction equation

HRID 1047161 reaction equation
[F:1][C:2]1[N:19]=[C:18]([F:20])[C:17]([I:21])=[CH:16][C:3]=1[C:4]([C:6](=[CH:12][N:13]([CH3:15])C)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[CH2:22]([N:24]1[CH2:28][CH2:27][CH2:26][C@H:25]1CN)[CH3:23]>C1COCC1>[F:1][C:2]1[N:19]=[C:18]([F:20])[C:17]([I:21])=[CH:16][C:3]=1[C:4]([C:6](=[CH:12][NH:13][CH2:15][C@@H:25]1[CH2:26][CH2:27][CH2:28][N:24]1[CH2:22][CH3:23])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 643457(S)-(-)-2-Aminomethyl-1-ethylpyrrolidineHCID 68750379HCID 68750379, compound2×

Product 1

HCID 178472022HCID 178472022, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2-(2,6-difluoro-5-iodonicotinoyl)-3-(dimethylamino)acrylate (Intermediate 37, 0.500 g, 1.10 mmol) was taken up THF (40 mL) and cooled to 0° C. for 10 min and then (S)-(1-ethylpyrrolidin-2-yl)methanamine (0.153 mL, 1.10 mmol) was added and stirred at room temperature for 2 min. The reaction mixture was quenched with sat NH4Cl diluted with EtOAc and separated, dried, and solvent removed. The residue was purified by a 0-5% gradient on the ISCO of DCM/Methanol to give (S)-ethyl 2-(2,6-difluoro-5-iodonicotinoyl)-3-((1-ethylpyrrolidin-2-yl)methylamino)acrylate (0.360 g, 67%) as a red oil.

Workup

  1. customThe reaction mixture was quenched with sat NH4Cl
  2. additiondiluted with EtOAc
  3. customseparated
  4. customdried
  5. customsolvent removed
  6. customThe residue was purified by a 0-5% gradient on the ISCO of DCM/Methanol

Sources & evidence

ORD record
ord-5c37cae89df24c88a7544463ded4b3f5
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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