Dimethylformamide → HCID 178440680, compound

HRID 1809122Notes

Reaction equation

HRID 1809122 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH2:12])[C:8]([NH2:11])=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([N:16]([CH:19]([CH3:21])[CH3:20])[CH2:17][CH3:18])(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:33]2N=C[CH:36]=[CH:37][C:32]=2N=N1.CN(C)C=[O:49]>C(OCC)(=O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]2[NH:11][C:36]([C:37]3[C:20]4[O:49][CH2:18][CH2:17][NH:16][C:19]=4[CH:21]=[CH:33][CH:32]=3)=[N:12][C:7]=2[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 4327084-Tert-butylbenzene-1,2-diamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 178440680HCID 178440680, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3.6 g (20 mmol) of 3,4-dihydro-2H-benzo[b][1,4]oxazin-8-carboxylic acid obtained in (1-4) was dissolved in 50 mL of dimethylformamide. 3.3 g (20 mmol) of 4-tert-butylbenzene-1,2-diamine, 7 mL (40 mmol) of diisopropylethylamine and 11 g (30 mmol) of O-(7-azabenzotriazole-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate were added thereto, and stirred for 3 hr at room temperature. The reaction mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, followed by drying over magnesium sulfate and concentrating under reduced pressure. The resulting residue was dissolved in acetate/toluene (45 mL/5 mL) and stirred for 4 hr at 70° C., followed by cooling to room temperature and concentrating under reduced pressure. The concentrate was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, followed by drying over magnesium sulfate and concentrating under reduced pressure. The obtained residue was subjected to column chromatography (ethyl acetate:hexane=1:1) to obtain the title compound (5.2 g, yield: 85%).

Workup

  1. washwashed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  2. dry with materialby drying over magnesium sulfate
  3. concentrationconcentrating under reduced pressure
  4. dissolutionThe resulting residue was dissolved in acetate/toluene (45 mL/5 mL)
  5. stirringstirred for 4 hr at 70° C.
  6. temperatureby cooling to room temperature
  7. concentrationconcentrating under reduced pressure
  8. dissolutionThe concentrate was dissolved in ethyl acetate
  9. washwashed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  10. dry with materialby drying over magnesium sulfate
  11. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-9fce1f4920b04b3fb5281417ede4071b
Source dataset
uspto-grants-2013_01
Patent number
US08362012B2

Reaction notes

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