Diisopropylethylamine → HCID 178440681, compound

HRID 912427Notes

Reaction equation

HRID 912427 reaction equation
O1CC[NH:4][C:3]2[CH:7]=[CH:8][CH:9]=[C:10](C(O)=O)[C:2]1=2.[C:14]([C:18]1[CH:19]=[C:20]([NH2:25])[C:21]([NH2:24])=[CH:22][CH:23]=1)([CH3:17])([CH3:16])[CH3:15].[CH:26](N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O.C(OC(=O)C)C.C(O)(=O)C.C1(C)C=CC=CC=1>[C:14]([C:18]1[CH:23]=[CH:22][C:21]2[NH:24][C:26]([C:9]3[CH:10]=[CH:2][C:3]([NH2:4])=[CH:7][CH:8]=3)=[N:25][C:20]=2[CH:19]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

8

Reactant 4

HCID 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)HCID 534038413,4-Dihydro-2H-1,4-benzoxazine-8-carboxylic acid

Product 1

HCID 178440681HCID 178440681, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 18331056Acetic acid tolueneSolvent

Procedure

To a solution of 3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxylic acid 3.6 g (20 mmol) of step 4 in dimethylformamide 50 mL were added 4-tert-butylbenzen-1,2-diamine 3.3 g (20 mmol), diisopropylethylamine 7 mL (40 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate 11 g (30 mmol), followed by stirring at room temperature for 3 hrs. The reaction mixture was diluted with ethylacetate, washed with a saturated sodium bicarbonate solution and a saturated NaCl solution, and dried over magnesium sulfate before being concentrated in a vacuum. The residue thus obtained was dissolved in acetic acid/toluene (45 mL/5 mL), stirred at 70° C. for 4 hrs, cooled to room temperature, and concentrated in a vacuum. The concentrate was dissolved in ethylacetate, washed with a saturated sodium bicarbonate solution and a saturated NaCl solution, and dried over magnesium sulfate before vacuum concentration. Purification by column chromatography (developing solvent: ethylacetate/hexane=1/1) gave 5.2 g of the title compound (yield 85%).

Workup

  1. washwashed with a saturated sodium bicarbonate solution
  2. dry with materiala saturated NaCl solution, and dried over magnesium sulfate
  3. concentrationbefore being concentrated in a vacuum
  4. customThe residue thus obtained
  5. stirringstirred at 70° C. for 4 hrs
  6. temperaturecooled to room temperature
  7. concentrationconcentrated in a vacuum
  8. dissolutionThe concentrate was dissolved in ethylacetate
  9. washwashed with a saturated sodium bicarbonate solution
  10. dry with materiala saturated NaCl solution, and dried over magnesium sulfate before vacuum concentration
  11. customPurification by column chromatography (developing solvent: ethylacetate/hexane=1/1)

Sources & evidence

ORD record
ord-7c9b97adc5e14950ae6f4e4506ce05e2
Source dataset
uspto-grants-2011_09
Patent number
US08026235B1

Reaction notes

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