Pyridine → HCID 136378681, compound

HRID 2278556Notes

Reaction equation

HRID 2278556 reaction equation
[Na].[CH3:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]2[N:10]=[C:11]([CH2:16][C:17]([OH:19])=O)[NH:12][C:13](=[O:15])[CH:14]=2)[CH2:4]1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl.CN(C)[CH2:29][CH2:30][CH2:31]N=C=NCC.[CH3:38]N(C=O)C>O>[CH3:38][C@H:25]1[CH2:24][C:23]2[C:22](=[CH:21][CH:29]=[CH:30][CH:31]=2)[N:20]1[C:17](=[O:19])[CH2:16][C:11]1[NH:12][C:13](=[O:15])[CH:14]=[C:9]([N:5]2[CH2:6][CH2:7][O:8][CH:3]([CH3:2])[CH2:4]2)[N:10]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5360545SodiumHCID 136378672HCID 136378672, compound

Product 1

HCID 136378681HCID 136378681, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 500 mg of the sodium salt of [4-(2-methylmorpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetic acid obtained above in 7.5 ml of DMF and 7.5 ml of pyridine is placed in a round-bottomed flask, and then 420 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 0.27 g of (S)-2-methyl-1H-indoline (CAS 22160-09-4) are added. The reaction mixture is stirred at ambient temperature for 48 h. 50 ml of water are added and the mixture is extracted with 3 times approximately 30 ml of ethyl acetate. The organic extracts are combined and successively washed with 30 ml of water, twice 30 ml of 1M hydrochloric acid solution and then 30 ml of saturated NaCl solution, dried over MgSO4 and concentrated under vacuum. The compound obtained is purified by chromatography on a 30 g Merck column (15-40 μm) at the flow rate of 30 ml/min, elution being carried out with dichloromethane/methanol from 98/2 to 95/5. The fractions containing the expected compound are combined and evaporated. (+)-2-[2-((S)-2-Methyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-methylmorpholin-4-yl)-3H-pyrimidin-4-one is isolated (237 mg), the characteristics of which are the following:

Workup

  1. customis placed in a round-bottomed flask
  2. extractionthe mixture is extracted with 3 times approximately 30 ml of ethyl acetate
  3. washsuccessively washed with 30 ml of water, twice 30 ml of 1M hydrochloric acid solution
  4. dry with material30 ml of saturated NaCl solution, dried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customThe compound obtained
  7. customis purified by chromatography on a 30 g Merck column (15-40 μm) at the flow rate of 30 ml/min, elution
  8. additionThe fractions containing the expected compound
  9. customevaporated

Sources & evidence

ORD record
ord-acd48fb4910b435aacc2cc3d217c7b13
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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