Diisopropylethylamine → HCID 178453343, compound

HRID 2408937Notes

Reaction equation

HRID 2408937 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.CCN(C(C)C)C(C)C.[C:16]([O:20][C:21]([NH:23][CH:24]([CH2:37][C:38]1([F:43])[CH2:42][CH2:41][CH2:40][CH2:39]1)[C:25]([NH:27][C:28]1([CH:32]([OH:36])[C:33](O)=[O:34])[CH2:31][CH2:30][CH2:29]1)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(Cl)Cl>[C:16]([O:20][C:21](=[O:22])[NH:23][CH:24]([C:25](=[O:26])[NH:27][C:28]1([CH:32]([OH:36])[C:33](=[O:34])[NH:1][C:2]2[CH:6]=[CH:5][NH:4][N:3]=2)[CH2:31][CH2:30][CH2:29]1)[CH2:37][C:38]1([F:43])[CH2:42][CH2:41][CH2:40][CH2:39]1)([CH3:19])([CH3:17])[CH3:18]

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 71073369HCID 71073369, compoundHCID 178418806HCID 178418806, compound

Product 1

HCID 178453343HCID 178453343, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Aminopyrazole (92 mg, 1.08 mmol) and DIEA (110 μL, 1.08 mmol) were added to a solution of compound 57-b (0.31 mmol) in anh. DMF (3 mL). The solution was cooled to 0° C. and stirred for 2-3 minutes, then HATU (126 mg, 0.32 mmol) in anh. DMF (1 mL) was added. The reaction mixture was allowed to attain room temperature, stirred for 16 h and then diluted with DCM. The organic phase was extracted with NaHCO3 sat. aq. solution. The aqueous phase was extracted with ethyl acetate and the combined organics dried over anh. Na2SO4 and then concentrated. Purification by flash column chromatography (MeOH/DCM, 0:1-2:8) gave the title compound (91 mg g, 63%). MS m/z 468.3 (M+H)+.

Workup

  1. customto attain room temperature
  2. stirringstirred for 16 h
  3. extractionThe organic phase was extracted with NaHCO3 sat. aq. solution
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. dry with materialthe combined organics dried over anh. Na2SO4
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (MeOH/DCM, 0:1-2:8)

Sources & evidence

ORD record
ord-79dafc93b59a4c9b9beec375cda33ad2
Source dataset
uspto-grants-2014_08
Patent number
US08815809B2

Reaction notes

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