Triethylamine → 3-(Formyl-methyl-amino)-1-{2-oxo-2-[4-(4-pyrimidin-2-yl-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-ethyl}-pyrrolidine-3-carboxylic acid methyl ester

HRID 1038098Notes

Reaction equation

HRID 1038098 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11]([C:13]1([N:18]([CH:20]=[O:21])[CH3:19])[CH2:17][CH2:16][NH:15][CH2:14]1)=[O:12].Cl[CH2:23][C:24]([N:26]1[CH2:31][CH:30]=[C:29]([C:32]2[CH:37]=[CH:36][C:35]([C:38]3[N:43]=[CH:42][CH:41]=[CH:40][N:39]=3)=[CH:34][CH:33]=2)[CH2:28][CH2:27]1)=[O:25]>O1CCOCC1>[CH3:9][O:10][C:11]([C:13]1([N:18]([CH:20]=[O:21])[CH3:19])[CH2:17][CH2:16][N:15]([CH2:23][C:24](=[O:25])[N:26]2[CH2:27][CH:28]=[C:29]([C:32]3[CH:33]=[CH:34][C:35]([C:38]4[N:39]=[CH:40][CH:41]=[CH:42][N:43]=4)=[CH:36][CH:37]=3)[CH2:30][CH2:31]2)[CH2:14]1)=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 589464332-Chloro-1-[4-(4-pyrimidin-2-yl-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanoneHCID 1317308893-(Formyl-methyl-amino)-pyrrolidine-3-carboxylic acid methyl ester, Hydrochloride2×

Product 1

HCID 589464693-(Formyl-methyl-amino)-1-{2-oxo-2-[4-(4-pyrimidin-2-yl-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-ethyl}-pyrrolidine-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Added triethylamine (0.3 ml, 2.15 mmol) to a solution of (3-(Formyl-methyl-amino)-pyrrolidine-3-carboxylic acid methyl ester, Hydrochloride.(4T) (90 mg, 0.405 mmol) and 2-Chloro-1-[4-(4-pyrimidin-2-yl-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone (140 mg, 0.447 mmol) in dioxane (5 ml) at room temperature, then stirred at 90° C. for 5 hours. The reaction was cooled and solvent evaporated yielding a residue which chromatographed on silica gel eluting with 7% MeOH/MeCl2 containing 2% NH4OH yielding 5T as a white solid (100 mg, 53%) ESMS (MH 464).

Workup

  1. temperatureThe reaction was cooled
  2. customsolvent evaporated
  3. customyielding a residue which
  4. customchromatographed on silica gel eluting with 7% MeOH/MeCl2 containing 2% NH4OH yielding 5T as a white solid (100 mg, 53%) ESMS (MH 464)

Sources & evidence

ORD record
ord-819ea873fe924700b653119f4724af4c
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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