Hydrochloric Acid → 3-[5-(4-Chloro-phenyl)-4-oxo-6-(4-pyrazin-2-yl-phenyl)-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzamidine

HRID 1024644Notes

Reaction equation

HRID 1024644 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=4)[C:21]#[N:22])[C:11]=3[N:10]=[C:9]2[C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[N:36][CH:35]=[CH:34][N:33]=3)=[CH:28][CH:27]=2)=[CH:4][CH:3]=1.Cl.C(=O)([O-])[O-].[NH4+:43].[NH4+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=4)[C:21]([NH2:43])=[NH:22])[C:11]=3[N:10]=[C:9]2[C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[N:36][CH:35]=[CH:34][N:33]=3)=[CH:28][CH:27]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 517111Ammonium CarbonateHCID 578993843-[5-(4-Chloro-phenyl)-4-oxo-6-(4-pyrazin-2-yl-phenyl)-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzonitrile

Product 1

HCID 578993963-[5-(4-Chloro-phenyl)-4-oxo-6-(4-pyrazin-2-yl-phenyl)-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzamidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At 0° C., 3-[5-(4-chloro-phenyl)-4-oxo-6-(4-pyrazin-2-yl-phenyl)-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzonitrile (prepared as described in example 47, 0.65 g, 1.29 mmol) is added to methanol saturated with hydrogen chloride gas (20 mL) with stirring. The reaction mixture is allowed to reach rt and stirred there for 40 h. The reaction mixture is then concentrated to a dry residue (0.7 g). It is taken in dry methanol (40 mL) and ammonium carbonate (1.15 g, 7.36 mmol) is added. After stirring at rt for 40 h, the reaction mixture is concentrated and the residue obtained is purified by column chromatography to afford 3-[5-(4-chloro-phenyl)-4-oxo-6-(4-pyrazin-2-yl-phenyl)-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzamidine. 1H NMR (DMSO-d6, 400 MHz) δ 9.25 (s, 1H), 8.71 (s, 1H), 8.63 (m, 1H), 8.55 (m, 2H), 8.29 (dd, 1H), 8.16 (s, 1H), 8.07 (m, 1H), 7.90 (m, 1H), 7.67 (m, 1H), 7.62 (m, 2H), 7.52 (m, 1H), 7.44 (m, 4H); LC-MS calculated for C28H19ClN8O (M+H+) 519.1, found 519.9.

Workup

  1. customto reach rt
  2. stirringstirred there for 40 h
  3. concentrationThe reaction mixture is then concentrated to a dry residue (0.7 g)
  4. stirringAfter stirring at rt for 40 h
  5. concentrationthe reaction mixture is concentrated
  6. customthe residue obtained
  7. customis purified by column chromatography

Sources & evidence

ORD record
ord-53ee51cd5df64bdab7483531c97fc021
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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