N-methyl-2-pyrrolidone → HCID 67520732, compound

HRID 1787004Notes

Reaction equation

HRID 1787004 reaction equation
O([C:8]1[C:20]2[N:19]3[C:14]([CH2:15][O:16][CH2:17][CH2:18]3)=[CH:13][C:12]=2[N:11]=[CH:10][N:9]=1)C1C=CC=CC=1.[NH2:21][C:22]1[CH:36]=[CH:35][C:25]([O:26][C:27]2[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=2)[C:30]#[N:31])=[C:24]([Cl:37])[CH:23]=1.Cl.N1C=CC=CC=1.CN1CCCC1=O>C(OCC)(=O)C>[ClH:37].[Cl:37][C:24]1[CH:23]=[C:22]([NH:21][C:8]2[C:20]3[N:19]4[C:14]([CH2:15][O:16][CH2:17][CH2:18]4)=[CH:13][C:12]=3[N:11]=[CH:10][N:9]=2)[CH:36]=[CH:35][C:25]=1[O:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[C:30]#[N:31]

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 10176127Pyridinium chlorideHCID 28401833HCID 28401833, compoundHCID 67521136HCID 67521136, compound

Product 1

HCID 67520732HCID 67520732, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-phenoxy-6,7-dihydro-9H-pyrimido[4′,5′:4,5]pyrrolo[2,1-c][1,4]oxazine (69 mg), 3-(4-amino-2-chlorophenoxy)benzonitrile (95 mg), pyridine hydrochloride (75 mg) and 1-methyl-2-pyrrolidone (1 mL) was stirred at 140° C. for 14 hrs. After the completion of the reaction, the mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate and saturated brine. The organic layer was dried over magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography (hexane/ethyl acetate=50/50→0/100). The obtained fractions were collected and concentrated, and the residue was dissolved in ethyl acetate (2 mL) and treated with 4N hydrochloric acid/ethyl acetate (0.13 mL) to give the title compound (81 mg) as hydrochloride crystals.

Workup

  1. customAfter the completion of the reaction
  2. washwashed with saturated aqueous sodium hydrogen carbonate and saturated brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customThe obtained fractions were collected
  6. concentrationconcentrated
  7. dissolutionthe residue was dissolved in ethyl acetate (2 mL)
  8. additiontreated with 4N hydrochloric acid/ethyl acetate (0.13 mL)

Sources & evidence

ORD record
ord-f54fe403840b4db7bc828ad07e9330b7
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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