Dimethylformamide → N-[2-[4,6-Bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridin-2-yl]ethyl]-N-isopropylurea

HRID 42603Notes

Reaction equation

HRID 42603 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH:12]=[C:11]2[C:6]([N:7]=[C:8]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[C:9]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[C:10]2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[N:5]1.[CH:33](N=C=O)([CH3:35])[CH3:34].C[N:40]([CH:42]=[O:43])C>>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:10]2[C:11]3[C:6](=[N:5][N:4]([CH2:3][CH2:2][N:1]([CH:33]([CH3:35])[CH3:34])[C:42]([NH2:40])=[O:43])[CH:12]=3)[N:7]=[C:8]([C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)[C:9]=2[C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 61277Isopropyl isocyanateHCID 670135732-(2-Aminoethyl)-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine

Product 1

HCID 68952500N-[2-[4,6-Bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridin-2-yl]ethyl]-N-isopropylureaYield 50%

Procedure

To a solution of 2-(2-aminoethyl)-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (0.06 g, 0.15 mmol, obtained in example 90) in DMF (1 mL), isopropylisocyanate (0.02 g, 0.18 mmol) was added under argon atmosphere. This was stirred at room temperature for 2 days. The solvent was concentrated again and diethyl ether was added to the residue obtained. The solvent was concentrated, to afford 38 mg of title compound in solid form (yield: 50%).

Workup

  1. concentrationThe solvent was concentrated again
  2. additiondiethyl ether was added to the residue
  3. customobtained
  4. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-3e582560370848ff8e4d8d0c8fbd6058
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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