HCID 9892671, compound → HCID 9805346, compound

HRID 1276364Notes

Reaction equation

HRID 1276364 reaction equation
[H][H].[Cl:3][C:4]1[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][C:5]=1[CH2:6][N:7]1[CH2:11][CH2:10][CH:9]([CH2:12][NH:13][C:14](=[O:32])[CH2:15][CH2:16][C:17]2[N:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=3)=[CH:19][N:18]=2)[CH2:8]1>CO.[Pd]>[Cl:3][C:4]1[C:36]([Cl:37])=[CH:35][CH:34]=[CH:33][C:5]=1[CH2:6][N:7]1[CH2:11][CH2:10][CH:9]([CH2:12][NH:13][C:14](=[O:32])[CH2:15][CH2:16][C:17]2[N:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=3)=[CH:21][N:22]=2)[CH2:8]1

Participants

5

Reactant 2

HCID 9892671HCID 9892671, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9805346HCID 9805346, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Hydrogen gas (balloon pressure) was introduced into a vessel containing Pd/C (10%, 100 mg, 0.1 mmol, 0.05 equiv.) in a solution of N-[1-(2,3-dichlorobenzyl)-pyrrolidin-3-(RS)-ylmethyl]-3-[5-(4-nitrophenyl)pyrimidin-2-yl]propionamide (1.0 g, 2.2 mmol) in methanol (30 mL). After 1.5 h, the reaction was terminated by purging with N2 and the reaction mixture was filtered through celite® and concentrated. The yellow residue was dissolved in ethyl acetate, then taken into the aqueous phase using 1 M hydrochloric acid. The aqueous phase was basified to pH 11, then extracted thoroughly with ethyl acetate. The organic fractions were combined and washed with brine, then dried sodium sulfate and concentrated to afford N-[1-(2,3-dichlorobenzyl)pyrrolidin-3-(RS)-ylmethyl]-3-[5-(4-aminophenyl)pyrimidin-2-yl]propionamide as a yellow crystalline solid (630 mg).

Workup

  1. customthe reaction was terminated
  2. customby purging with N2
  3. filtrationthe reaction mixture was filtered through celite®
  4. concentrationconcentrated
  5. dissolutionThe yellow residue was dissolved in ethyl acetate
  6. extractionextracted thoroughly with ethyl acetate
  7. washwashed with brine
  8. concentrationdried sodium sulfate and concentrated

Sources & evidence

ORD record
ord-5069fe6736774e3f8e2ed0445383926a
Source dataset
uspto-grants-2000_12
Patent number
US06166015

Reaction notes

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