Diisopropylethylamine → HCID 89700078, compound

HRID 1055750Notes

Reaction equation

HRID 1055750 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N:9]1[C:16]2[N:12]([N:13]=[C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:15]=2)[CH:11]=[CH:10]1.[Br:23][C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([S:33]([F:38])([F:37])([F:36])([F:35])[F:34])[CH:32]=1)[C:27](O)=[O:28].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[Br:23][C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([S:33]([F:38])([F:34])([F:35])([F:36])[F:37])[CH:32]=1)[C:27]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([CH3:1])=[C:3]([N:9]2[C:16]3[N:12]([N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[CH:11]=[CH:10]2)[CH:4]=1)=[O:28]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58137421HCID 58137421, compoundHCID 897000234-Methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]aniline

Product 1

HCID 89700078HCID 89700078, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

10.0 g (34.6 mmol) of the compound of Example 6A and 11.3 g (34.6 mmol) of the compound of Example 15A were dissolved in 120 ml anhydrous DMF, and 15.8 g (41.5 mmol) of HATU and 7.2 ml (41.5 mmol) of N,N-diisopropylethylamine were added in succession. The reaction mixture was stirred at RT overnight (about 15 h) and then stirred into 1.6 liters of water. After 40 minutes, the resulting precipitate was filtered off with suction, washed thoroughly with a further 0.5 liter of water and finally dissolved in 1.8 liters of ethyl acetate. The organic solution was washed successively with water and saturated sodium chloride solution. After drying over anhydrous magnesium sulphate, the mixture was filtered and the solvent was removed on a rotary evaporator. The crude product obtained in this manner was purified by filtration with suction (about 330 g of silica gel, mobile phase gradient cyclohexane/ethyl acetate 1:1→1:3). This gave 11.95 g (57% of theory) of the title compound.

Workup

  1. waitAfter 40 minutes
  2. filtrationthe resulting precipitate was filtered off with suction
  3. washwashed thoroughly with a further 0.5 liter of water
  4. dissolutionfinally dissolved in 1.8 liters of ethyl acetate
  5. washThe organic solution was washed successively with water and saturated sodium chloride solution
  6. dry with materialAfter drying over anhydrous magnesium sulphate
  7. filtrationthe mixture was filtered
  8. customthe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-927cdbba178745d192e54ef2ac71e28d
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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