Diisopropylethylamine → N-(3-(2-methylthiazol-4-yl)phenyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide

HRID 2383457Notes

Reaction equation

HRID 2383457 reaction equation
FC(F)(F)C([O-])=O.[CH:8]1[C:20]2[C:19]3[CH2:18][CH2:17][NH2+:16][CH2:15][C:14]=3[CH:13]=[N:12][C:11]=2[NH:10][N:9]=1.CCN(C(C)C)C(C)C.[N:30]([C:33]1[CH:34]=[C:35]([C:39]2[N:40]=[C:41]([CH3:44])[S:42][CH:43]=2)[CH:36]=[CH:37][CH:38]=1)=[C:31]=[O:32]>C1COCC1>[CH3:44][C:41]1[S:42][CH:43]=[C:39]([C:35]2[CH:34]=[C:33]([NH:30][C:31]([N:16]3[CH2:15][C:14]4[CH:13]=[N:12][C:11]5[NH:10][N:9]=[CH:8][C:20]=5[C:19]=4[CH2:18][CH2:17]3)=[O:32])[CH:38]=[CH:37][CH:36]=2)[N:40]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 49612614-(3-Isocyanatophenyl)-2-methyl-1,3-thiazoleHCID 866455766,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium 2,2,2-trifluoroacetate

Product 1

HCID 59490779N-(3-(2-methylthiazol-4-yl)phenyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamideYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium 2,2,2-trifluoroacetate (0.100 g, 0.25 mmol) in THF (5 mL) and Hunig's Base (0.26 mL, 1.50 mmol) was added 4-(3-isocyanatophenyl)-2-methylthiazole (0.0567 g, 0.25 mmol). The reaction was shaken at room temperature for 2 hours. The solvent was then removed under reduced pressure followed by addition of 1 M Na2CO3 (5 mL) and EtOAc (10 mL). The organic layer was separated, washed with water (3×10 mL) followed by adding water (10 mL). The EtOAC was then removed under reduced pressure. A white solid crashed out which was filtered, washed with water, dried under reduced pressure to give the pure desired product, N-(3-(2-methylthiazol-4-yl)phenyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide as a white solid (0.069 g, 71%).

Workup

  1. customThe solvent was then removed under reduced pressure
  2. additionfollowed by addition of 1 M Na2CO3 (5 mL) and EtOAc (10 mL)
  3. customThe organic layer was separated
  4. washwashed with water (3×10 mL)
  5. additionby adding water (10 mL)
  6. customThe EtOAC was then removed under reduced pressure
  7. filtrationwas filtered
  8. washwashed with water
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-d469849fa5154a11a5f45a843f94e87e
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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