Diisopropylethylamine → HCID 57734262, compound

HRID 912777Notes

Reaction equation

HRID 912777 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][CH:11]([C:14](O)=O)[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:17][C:18]1[CH:19]=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:21]=[CH:22][C:23]=1[NH2:24].C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C=O)C>[Cl:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[NH:17][C:18]4[CH:19]=[C:20]([C:25]([F:26])([F:27])[F:28])[CH:21]=[CH:22][C:23]=4[N:24]=3)[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5208224-Trifluoromethyl-1,2-phenylenediamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 18071053HCID 18071053, compound

Product 1

HCID 57734262HCID 57734262, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the acid from step (b) above (0.48 g, 2 mmol) in DMF (20 mL) was added 3,4-diaminobenzotrifluoride (0.354 g, 2 mmol, Lancaster), followed by N,N-diisopropylethylamine (0.516 g, 4 mmol, Aldrich) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.912 g, 2.4 mmol, Aldrich). The reaction mixture was stirred at room temperature for 16 h, and then concentrated in vacuo. The residue was dissolved in EtOAc and the organic solution was washed with saturated NaHCO3 and brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with hexane/EtOAc (3:7) to give the title compound as a purple solid. MS (ESI, pos. ion) m/z: 399 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washthe organic solution was washed with saturated NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with hexane/EtOAc (3:7)

Sources & evidence

ORD record
ord-1d4b87e7e5ed451ab4d1c63fb3d02514
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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