Hydrochloric Acid → 1-(4-Fluoro-2,3-dihydroindol-1-yl)-2-(4-methoxy-6-chloropyrimidin-2-yl)ethanone

HRID 2278531Notes

Reaction equation

HRID 2278531 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.[Na].[CH3:24][O:25][C:26]1[CH:31]=[C:30]([Cl:32])[N:29]=[C:28]([CH2:33][C:34](O)=[O:35])[N:27]=1.Cl>CN(C=O)C.N1C=CC=CC=1.C(OCC)C.O.C(OCC)(=O)C>[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:34](=[O:35])[CH2:33][C:28]1[N:27]=[C:26]([O:25][CH3:24])[CH:31]=[C:30]([Cl:32])[N:29]=1

Participants

11

Reactant 5

HCID 313Hydrochloric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5360545SodiumHCID 12420761(4-Chloro-6-methoxypyrimidin-2-yl)acetic acidHCID 162444404-Fluoro-2,3-dihydro-1H-indole

Product 1

HCID 866992651-(4-Fluoro-2,3-dihydroindol-1-yl)-2-(4-methoxy-6-chloropyrimidin-2-yl)ethanone

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.32 g of 4-fluoro-2,3-dihydro-1H-indole and 5.56 g of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride are added to a solution of 5.4 g of the sodium salt of (4-methoxy-6-chloropyrimidin-2-yl)acetic acid in 50 ml of DMF and 4.3 ml of pyridine. The reaction medium is stirred at ambient temperature for one hour. 200 ml of ethyl acetate and 100 ml of water are added, and also 1N hydrochloric acid to pH=5-6. After settling out, the organic phase is dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The oil obtained is taken up with ethyl ether. The solid formed is filtered off so as to give 2.2 g of 1-(4-fluoro-2,3-dihydroindol-1-yl)-2-(4-methoxy-6-chloropyrimidin-2-yl)ethanone in the form of an orangey-colored solid, the characteristics of which are the following:

Workup

  1. dry with materialthe organic phase is dried over magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe oil obtained
  5. customThe solid formed
  6. filtrationis filtered off so as

Sources & evidence

ORD record
ord-89227cdda80b4de69f572f596545ec28
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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