Hydrochloric Acid → 3-[6-[4-(6-Ammo-pyridin-3-yl)-phenyl]-5-(4-chloro-phenyl)-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzamidine

HRID 1024619Notes

Reaction equation

HRID 1024619 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]([C:32]4[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=4)[C:16](=[O:31])[C:17]4[CH:22]=[N:21][N:20]([C:23]5[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=5)[C:26]#[N:27])[C:18]=4[N:19]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.C(=O)([O-])[O-].[NH4+:44].[NH4+]>CO>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]3[N:15]([C:32]4[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=4)[C:16](=[O:31])[C:17]4[CH:22]=[N:21][N:20]([C:23]5[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=5)[C:26]([NH2:44])=[NH:27])[C:18]=4[N:19]=3)=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 517111Ammonium CarbonateHCID 578994223-[6-[4-(6-Amino-pyridin-3-yl)-phenyl]-5-(4-chloro-phenyl)-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzonitrile

Product 1

HCID 578994283-[6-[4-(6-Ammo-pyridin-3-yl)-phenyl]-5-(4-chloro-phenyl)-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzamidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At 0° C., 3-[6-[4-(6-amino-pyridin-3-yl)-phenyl]-5-(4-chloro-phenyl)-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzonitrile (prepared as described in example 28, 0.325 g, 0.629 mmol) is added to methanol saturated with hydrogen chloride gas (7 mL) with stirring. The reaction mixture is allowed to reach rt and stirred there for 24 h. The reaction mixture is then concentrated to a dry residue. It is taken in dry methanol (6 mL) and ammonium carbonate (0.593 g, 3.77 mmol) is added. After stirring at rt for 16 h, the reaction mixture is concentrated and the residue obtained is purified by preparative HPLC to afford 3-[6-[4-(6-ammo-pyridin-3-yl)-phenyl]-5-(4-chloro-phenyl)-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzamidine. 1H NMR (Acetone-d6, 400 MHz) δ 11.32 (br, 2H), 8.88 (br, 2H), 8.72 (m, 2H), 8.40 (s, 1H), 8.25 (m, 2H), 7.95 (m, 2H), 7.83 (m, 1H), 7.65 (m, 5H), 7.45 (m, 4H), 7.14 (d, 1H); LC-MS calculated for C29H21ClN8O (M+H+) 533.2, found 533.1.

Workup

  1. customto reach rt
  2. stirringstirred there for 24 h
  3. concentrationThe reaction mixture is then concentrated to a dry residue
  4. stirringAfter stirring at rt for 16 h
  5. concentrationthe reaction mixture is concentrated
  6. customthe residue obtained
  7. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-e74935bd185948bfaa40633a6f6a1baa
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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