Dimethyl Sulfoxide → 1-ethyl-N-(4-pyridinylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 613274Notes

Reaction equation

HRID 613274 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15](Cl)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2].CS(C)=O.[NH2:21][CH2:22][C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1.[NH4+].[OH-]>O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:21][CH2:22][C:23]4[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14923Ammonium HydroxideHCID 773174-PyridinemethanamineHCID 158169081-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 195922291-ethyl-N-(4-pyridinylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amineYield 34.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 1-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline (1.0 g, 4.3 mmol), DMSO (3 ml) and 4-(aminomethyl)pyridine (0.92 ml, 9 mmol) was heated at 80-90° C. overnight. The reaction mixture was poured into water (200 ml)/NH4OH (1 ml) and the mixture was extracted with CH2Cl2 (3×100 ml). The CH2Cl2 layers were combined, dried over MgSO4 and evaporated. The residue was crystallized from ethyl acetate and recrystallized from ethyl acetate to afford 450 mg of 1-ethyl-N-(4-pyridinylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, m.p. 191-192° C.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (3×100 ml)
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue was crystallized from ethyl acetate
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ce6785af9f4c4e81b4e824e187b0395c
Source dataset
uspto-grants-1999_12
Patent number
US06008226

Reaction notes

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