Dimethylformamide → HCID 178522790, compound

HRID 1625428Notes

Reaction equation

HRID 1625428 reaction equation
C[Si](C)(C)CCOC[N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[C:9]([C:16]2[S:20][C:19]([CH2:21][NH2:22])=[CH:18][CH:17]=2)=[N:8]1.[F:25][C:26]1[CH:27]=[C:28]([CH:40]=[CH:41][C:42]=1[F:43])[CH2:29][N:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36](O)=[O:37])[C:31]1=[O:39].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C)C=O.C(N(CC)C(C)C)(C)C>C(O)(=O)CC(CC(O)=O)(C(O)=O)O.O>[NH:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[C:9]([C:16]2[S:20][C:19]([CH2:21][NH:22][C:36]([C:32]3[C:31](=[O:39])[N:30]([CH2:29][C:28]4[CH:40]=[CH:41][C:42]([F:43])=[C:26]([F:25])[CH:27]=4)[CH:35]=[CH:34][CH:33]=3)=[O:37])=[CH:18][CH:17]=2)=[N:8]1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 534279691-(3,4-Difluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acidHCID 68607503C-{5-[1-(2-Trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-thiophen-2-yl}-methylamine

Product 1

HCID 178522790HCID 178522790, compound

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 962WaterSolvent

Procedure

C-{5-[1-(2-Trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-thiophen-2-yl}-methylamine (23 mg, 0.000064 mol), 1-(3,4-difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid (2.0E1 mg, 0.000075 mol) and HATU (44 mg, 0.00012 mol; Applied Biosystems) were dissolved in N,N-dimethylformamide (1.25 mL, 0.0161 mol; Acros). To this was added N,N-diisopropylethylamine (56 uL, 0.00032 mol; Aldrich) and the reaction was stirred for 1 hour at room temperature. The reaction was diluted with 5% citric acid in water, then extracted with ethyl acetate. Saturated sodium chloride was added to aid separation. The organic layer was washed with saturated sodium chloride, dried with sodium sulfate, filtered and evaporated to yield the crude title compound. MS m/z=608.34 (M+1).

Workup

  1. extractionextracted with ethyl acetate
  2. additionSaturated sodium chloride was added
  3. customseparation
  4. washThe organic layer was washed with saturated sodium chloride
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-9c8ecf8a04804a4db8f630c4134e98b2
Source dataset
uspto-grants-2014_07
Patent number
US08778977B2

Reaction notes

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