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Water → N-[5-(Pyrido[3,2-e]pyrrolo[1,2-a]pyrazin-5(6H)ylcarbonyl)-2-pyridinyl]-5-fluoro-2-methylbenzamide

HRID 976409
Notes
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Reaction equation

HRID 976409 reaction equation
[N:1]1[C:10]2[N:9]3[CH:11]=[CH:12][CH:13]=[C:8]3[CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[F:21][C:22]1[CH:23]=[CH:24][C:25]([CH3:40])=[C:26]([CH:39]=1)[C:27]([NH:29][C:30]1[N:35]=[CH:34][C:33]([C:36](Cl)=[O:37])=[CH:32][CH:31]=1)=[O:28].O>ClCCl>[N:1]1[C:10]2[N:9]3[CH:11]=[CH:12][CH:13]=[C:8]3[CH2:7][N:6]([C:36]([C:33]3[CH:32]=[CH:31][C:30]([NH:29][C:27](=[O:28])[C:26]4[CH:39]=[C:22]([F:21])[CH:23]=[CH:24][C:25]=4[CH3:40])=[N:35][CH:34]=3)=[O:37])[C:5]=2[CH:4]=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 155082506-(5-Fluoro-2-methylbenzoyl)aminopyridine-3-carbonyl chlorideHCID 189175145,6-Dihydropyrido[3,2-e]pyrrolo[1,2-a]pyrazine

Product 1

HCID 18917537N-[5-(Pyrido[3,2-e]pyrrolo[1,2-a]pyrazin-5(6H)ylcarbonyl)-2-pyridinyl]-5-fluoro-2-methylbenzamideYield 44.4%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent2×

Procedure

To a chilled (0° C.) solution of 0.343 g of 5,6-dihydropyrido[3,2-e]pyrrolo[1,2-a]pyrazine and 1.1 ml of triethylamine in 5 ml of dichloromethane is added 1.17 g of 6-(5-fluoro-2-methylbenzoyl)aminopyridine-3-carbonyl chloride. The mixture is stirred at room temperature for 16 hours. To the mixture is added 50 ml of dichloromethane and 20 ml of water. The organic layer is separated and washed with 20 ml each of 1M NaHCO3 and brine. The organic layer is dried (Na2SO4) and passed through a thin pad of hydrous magnesium silicate and the pad washed with dichloromethane. The filtrate is concentrated and the residue chromatographed on silica gel prep-plates with ethyl acetate-hexane (1:1) as eluent. The product is crystallized from ethyl acetate to give 0.38 g of white crystals, m.p. 226°-234° C.

Workup

  1. customThe organic layer is separated
  2. washwashed with 20 ml each of 1M NaHCO3 and brine
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. washthe pad washed with dichloromethane
  5. concentrationThe filtrate is concentrated
  6. customthe residue chromatographed on silica gel prep-plates with ethyl acetate-hexane (1:1) as eluent
  7. customThe product is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-ceba62f16aee4e48966fd362452e35df
Source dataset
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05612334

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes