1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 1-(4-Fluoro-2,3-dihydroindol-1-yl)-2-(4-methoxy-6-morpholin-4-ylpyrimidin-2-yl)ethanone

HRID 2278584Notes

Reaction equation

HRID 2278584 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][NH:6]2.Cl.CN(C)CCCN=C=NCC.[CH3:23][O:24][C:25]1[CH:30]=[C:29]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[N:28]=[C:27]([CH2:37][C:38]([O-])=[O:39])[N:26]=1.[Na+]>CN(C=O)C.N1C=CC=CC=1>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][N:6]2[C:38](=[O:39])[CH2:37][C:27]1[N:26]=[C:25]([O:24][CH3:23])[CH:30]=[C:29]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[N:28]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 162444404-Fluoro-2,3-dihydro-1H-indoleHCID 86699277Sodium (4-methoxy-6-morpholin-4-ylpyrimidin-2-yl)acetate

Product 1

HCID 682817151-(4-Fluoro-2,3-dihydroindol-1-yl)-2-(4-methoxy-6-morpholin-4-ylpyrimidin-2-yl)ethanone

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

1.2 g of 4-fluoro-2,3-dihydro-1H-indole and 1.9 g of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride are added to a solution of 1.7 g of sodium (4-methoxy-6-morpholin-4-ylpyrimidin-2-yl)acetate in 15 ml of DMF and 5 ml of pyridine. The reaction medium is stirred at ambient temperature for 3 hours. The reaction mixture is concentrated under reduced pressure and then diluted in 80 ml of water and 15 ml of ethyl acetate. The precipitate formed is washed with 15 ml of ethyl ether and then with 15 ml of petroleum ether. After drying under reduced pressure, 1.53 g of 1-(4-fluoro-2,3-dihydroindol-1-yl)-2-(4-methoxy-6-morpholin-4-ylpyrimidin-2-yl)ethanone are obtained in the form of a pink solid used as it is in the next step.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. additiondiluted in 80 ml of water
  3. customThe precipitate formed
  4. washis washed with 15 ml of ethyl ether
  5. dry with materialAfter drying under reduced pressure, 1.53 g of 1-(4-fluoro-2,3-dihydroindol-1-yl)-2-(4-methoxy-6-morpholin-4-ylpyrimidin-2-yl)ethanone
  6. customare obtained in the form of a pink solid

Sources & evidence

ORD record
ord-5051c841cea94fc19d76041cbab5c362
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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