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3-Chloro-4-fluoroaniline → Ethyl 4-[(3-chloro-4-fluorophenyl)amino]-5,8-dihydropyrido[4',3':4,5]furo[2,3-d]pyrimidine-7(6H)-carboxylate

HRID 38534
Notes
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Reaction equation

HRID 38534 reaction equation
[C:1]([C:3]1[C:11]2[CH2:10][CH2:9][N:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:7][C:6]=2[O:5][C:4]=1/[N:17]=[CH:18]/[N:19](C)C)#[N:2].[Cl:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][C:29]=1[F:30])N>C(#N)C.C(O)(=O)C>[Cl:22][C:23]1[CH:24]=[C:25]([NH:2][C:1]2[C:3]3[C:11]4[CH2:10][CH2:9][N:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:7][C:6]=4[O:5][C:4]=3[N:17]=[CH:18][N:19]=2)[CH:27]=[CH:28][C:29]=1[F:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 58116902ethyl 3-cyano-2-[(E)-dimethylaminomethylideneamino]-5,7-dihydro-4H-furo[2,3-c]pyridine-6-carboxylate

Product 1

HCID 58116794Ethyl 4-[(3-chloro-4-fluorophenyl)amino]-5,8-dihydropyrido[4',3':4,5]furo[2,3-d]pyrimidine-7(6H)-carboxylateYield 22.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent
HCID 6342
Acetonitrile
Solvent

Procedure

Ethyl 3-cyano-2-{[(1E)-(dimethylamino)methylidene]amino}-4,7-dihydrofuro[2,3-c]pyridine-6(5H)-carboxylate from Example 37A (1.20 g, 4.14 mmol) and 3-chloro-4-fluoroaniline (1.20 g, 8.27 mmol) were heated in a mixture of acetonitrile (20 mL) and acetic acid (10 mL) in a microwave oven for 30 min to 160° C. The mixture was then concentrated in vacuo, diluted with water, basified with aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and the solvent was evaporated. The residue was triturated with dichloromethane and left to stand for 20 h. The precipitate was collected by suction filtration. Subsequently, the solid was triturated with methanol. The crystals were collected by suction filtration and washed with diethyl ether to yield 360 mg (22%) of the title compound. A second batch of 159 mg (10%) was obtained from the mother liquor after purification by preparative HPLC.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was triturated with dichloromethane
  7. waitleft
  8. filtrationThe precipitate was collected by suction filtration
  9. customSubsequently, the solid was triturated with methanol
  10. filtrationThe crystals were collected by suction filtration
  11. washwashed with diethyl ether

Sources & evidence

ORD record
ord-e3fb2485ce874a8fa86fc9d0b8d0056b
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524722B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes