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

HRID 1038053Notes

Reaction equation

HRID 1038053 reaction equation
[C:1](O)(=O)[CH:2](C(C(O)=O)O)[OH:3].[CH3:11][O:12][C:13]([C:15]1([CH2:20][O:21][CH3:22])[CH2:19][CH2:18][NH:17][CH2:16]1)=[O:14].ClCC([N:27]1[CH2:32][CH:31]=[C:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]3[N:44]=[CH:43][CH:42]=[CH:41][N:40]=3)=[CH:35][CH:34]=2)[CH2:29][CH2:28]1)=O.C(N(CC)CC)C>C(#N)C>[CH3:11][O:12][C:13]([C:15]1([CH2:20][O:21][CH3:22])[CH2:19][CH2:18][N:17]([C:2](=[O:3])[CH2:1][N:27]2[CH2:32][CH:31]=[C:30]([C:33]3[CH:38]=[CH:37][C:36]([C:39]4[N:44]=[CH:43][CH:42]=[CH:41][N:40]=4)=[CH:35][CH:34]=3)[CH2:29][CH2:28]2)[CH2:16]1)=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 589464332-Chloro-1-[4-(4-pyrimidin-2-yl-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanoneHCID 689606333-Methoxymethyl-pyrrolidine-3-carboxylic acid methyl ester tartaric acid salt

Product 1

HCID 674196363-Methoxymethyl-1-{2-[4-(4-pyrimidin-2-yl-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-acetyl}-pyrrolidine-3-carboxylic acid methyl esterYield 68.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Methoxymethyl-pyrrolidine-3-carboxylic acid methyl ester tartaric acid salt 1.54 gm, 4.85 mmol) in 25 ml of acetonitrile was added 2-Chloro-1-[4-(4-pyrimidin-2-yl-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone (2.2 gm, 5.82 mmol), triethylamine (3.4 ml, 24.3 mmol) and the reaction mixture stirred at 80 C for 18 hrs. The reaction mixture was evaporated, and extracted into dichloromethane from water. The dichloromethane extracts were dried over Na2SO4, filtered and evaporated. The mixture was chromatographed on silica gel using 2-3% MeOH/dichlormethane to obtain 1.5 gm of title compound.

Workup

  1. customThe reaction mixture was evaporated
  2. extractionextracted into dichloromethane from water
  3. dry with materialThe dichloromethane extracts were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe mixture was chromatographed on silica gel using 2-3% MeOH/dichlormethane

Sources & evidence

ORD record
ord-b0b66aa7bb0d45b28818d7c797a1cad5
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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