Pyridine → HCID 68281700, compound

HRID 2278573Notes

Reaction equation

HRID 2278573 reaction equation
Cl.CN(C)CCCN=C=NCC.N1C=CC=CC=1.[CH3:19][N:20]1[C:25](=[O:26])[CH:24]=[C:23]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[N:22]=[C:21]1[CH2:33][C:34]([O-:36])=O.[Na+].[F:38][C:39]1[CH:47]=[CH:46][CH:45]=[C:44]2[C:40]=1[CH2:41][CH:42]([CH3:48])[NH:43]2>CN(C)C=O.C(OCC)(=O)C.O>[F:38][C:39]1[CH:47]=[CH:46][CH:45]=[C:44]2[C:40]=1[CH2:41][CH:42]([CH3:48])[N:43]2[C:34](=[O:36])[CH2:33][C:21]1[N:20]([CH3:19])[C:25](=[O:26])[CH:24]=[C:23]([N:27]2[CH2:28][CH2:29][O:30][CH2:31][CH2:32]2)[N:22]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 573882254-fluoro-2-methyl-2,3-dihydro-1H-indoleHCID 57523684Sodium [1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate

Product 1

HCID 68281700HCID 68281700, compoundYield 29.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.19 g of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 120 μl of pyridine are added to a solution of 0.22 g of sodium [1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate (prepared in step 2c of example 4c) in 3 ml of N,N-dimethylformamide. The resulting suspension is stirred at ambient temperature for 15 minutes and then 0.11 g of (+)-4-fluoro-2-methyl-2,3-dihydro-1H-indole [reference example 8c, step 6c] is rapidly added. The reaction mixture is stirred at ambient temperature for 64 hours and is then treated with a mixture of 20 ml of water and 2 ml of ethyl acetate, and then stirred at ambient temperature for 2 hours. The precipitate formed is filtered off, and then rinsed successively with 3 ml of water and 3×6 ml of diethyl ether. The solid obtained is dried with suction, then dried under reduced pressure at 40° C. 82 mg of (−)-2-{2-[4-fluoro-2-methyl-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-3-methyl-6-(morpholin-4-yl)pyrimidin-4(3H)-one are thus obtained in the form of a white solid, the characteristics of which are the following:

Workup

  1. stirringThe reaction mixture is stirred at ambient temperature for 64 hours
  2. stirringstirred at ambient temperature for 2 hours
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. washrinsed successively with 3 ml of water and 3×6 ml of diethyl ether
  6. customThe solid obtained
  7. customis dried with suction
  8. customdried under reduced pressure at 40° C

Sources & evidence

ORD record
ord-57440908c800465b88aa181e2cf034f2
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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