HCID 68515035, compound → N1-(1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)-2-fluoro-N1-(2-morpholinoethyl)benzene-1,4-diamine

HRID 2241438Notes

Reaction equation

HRID 2241438 reaction equation
[CH3:1][O:2][C:3]1[CH:37]=[CH:36][C:6]([CH2:7][N:8]2[C:12]3[N:13]=[CH:14][CH:15]=[C:16]([N:17]([C:26]4[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][C:27]=4[F:35])[CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[C:11]=3[CH:10]=[N:9]2)=[CH:5][CH:4]=1>CCO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([N:17]([CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[C:26]4[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][C:27]=4[F:35])=[C:11]3[CH:10]=[N:9]2)=[CH:36][CH:37]=1

Participants

3

Reactant 1

HCID 68515035HCID 68515035, compound

Product 1

HCID 68514133N1-(1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)-2-fluoro-N1-(2-morpholinoethyl)benzene-1,4-diamineYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-methoxybenzyl)-N-(2-fluoro-4-nitrophenyl)-N-(2-morpholinoethyl)-1H-pyrazolo[3,4-b]pyridin-4-amine (0.024 g, 0.0474 mmol) and SnCl2-dihydrate (0.0535 g, 0.237 mmol) were stirred in EtOH (2 mL) for 2 hours at reflux. The reaction was cooled to room temperature and then concentrated under reduced pressure and dried in vacuo. The residue was diluted with EtOAc and washed with saturated Na2CO3 (20 mL). The organics were dried over Na2SO4. The organics were filtered and concentrated to give 21 mg (92%) of product as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.21 (d, 1H), 7.27 (m, 2H), 7.11 (m, 1H), 6.558 (bs, 1H), 6.49 (m, 2H), 6.29 (d, 1H), 5.48 (s, 2H), 4.12 (m, 4H), 3.73 (s, 3H), 3.69 (m, 4H), 2.73 (t, 2H), 2.48 (m, 4H); F NMR (400 MHz, CDCl3) −120.43 (s, 1F); LRMS (apci pos): 477.3 (M+H)+.

Workup

  1. temperatureat reflux
  2. concentrationconcentrated under reduced pressure
  3. customdried in vacuo
  4. additionThe residue was diluted with EtOAc
  5. washwashed with saturated Na2CO3 (20 mL)
  6. dry with materialThe organics were dried over Na2SO4
  7. filtrationThe organics were filtered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b1c5a57e9d184f90b8adadab40474e6c
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

Loading…