2-Chloronicotinic acid → 5-Acetyl-1-(1,3-benzodioxol-5-yl)-8-{[(2-chloropyridin-3-yl)carbonyl]amino}-4,5-dihydro-1h-pyrazolo[4,3-c]quinoline-3-carboxamide

HRID 1348925Notes

Reaction equation

HRID 1348925 reaction equation
C(O)(=O)C.[C:5]([N:8]1[C:17]2[CH:16]=[CH:15][C:14]([NH2:18])=[CH:13][C:12]=2[C:11]2[N:19]([C:25]3[CH:33]=[CH:32][C:28]4[O:29][CH2:30][O:31][C:27]=4[CH:26]=3)[N:20]=[C:21]([C:22]([NH2:24])=[O:23])[C:10]=2[CH2:9]1)(=[O:7])[CH3:6].[Cl:34][C:35]1[N:43]=[CH:42][CH:41]=[CH:40][C:36]=1[C:37](O)=[O:38].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:5]([N:8]1[C:17]2[CH:16]=[CH:15][C:14]([NH:18][C:37]([C:36]3[C:35]([Cl:34])=[N:43][CH:42]=[CH:41][CH:40]=3)=[O:38])=[CH:13][C:12]=2[C:11]2[N:19]([C:25]3[CH:33]=[CH:32][C:28]4[O:29][CH2:30][O:31][C:27]=4[CH:26]=3)[N:20]=[C:21]([C:22]([NH2:24])=[O:23])[C:10]=2[CH2:9]1)(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 762582-Chloronicotinic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 101388555-Acetyl-8-amino-1-(1,3-benzodioxol-5-yl)-4,5-dihydro-1h-pyrazolo[4,3-c]quinoline-3-carboxamide acetate

Product 1

HCID 101432155-Acetyl-1-(1,3-benzodioxol-5-yl)-8-{[(2-chloropyridin-3-yl)carbonyl]amino}-4,5-dihydro-1h-pyrazolo[4,3-c]quinoline-3-carboxamideYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title material of Example 17 (100 mg, 0.00025 mol) was dissolved in DMF (2 mL), and to the solution was added 2-Chloronicotinic acid (40 mg, 0.00025 mol), HATU (144 mg, 0.00038 mol), and DIEA (49 mg, 0.00038 mol). The reaction was blanketed with argon and stirred at room temperature for 18 hours. The solution was concentrated in vacuo, and the resulting solid were washed with water and then filtered. The product was then recrystallized from ethanol, and isolated by vacuum filtration. 25 mg. (MW=530.93, 19% yield). LC/MS m/z=531.7 (m+1).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. washthe resulting solid were washed with water
  3. filtrationfiltered
  4. customThe product was then recrystallized from ethanol
  5. customisolated by vacuum filtration

Sources & evidence

ORD record
ord-f406e9171fef4485be4c59aa2b741cc2
Source dataset
uspto-grants-2007_05
Patent number
US07211597B2

Reaction notes

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