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

HRID 1024620Notes

Reaction equation

HRID 1024620 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][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)=[N:6][CH:7]=1.Cl.C(=O)([O-])[O-].[NH4+:44].[NH4+]>CO>[NH2:1][C:2]1[CH:3]=[CH:4][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)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 517111Ammonium CarbonateHCID 578994433-[6-[4-(5-Amino-pyridin-2-yl)-phenyl]-5-(4-chloro-phenyl)-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzonitrile

Product 1

HCID 578993613-[6-[4-(5-Amino-pyridin-2-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-(5-amino-pyridin-2-yl)-phenyl]-5-(4-chloro-phenyl)-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzonitrile (prepared as described in example 27, 0.30 g, 0.58 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 30 h. The reaction mixture is then concentrated to a dry residue. It is taken in dry methanol (6 mL) and ammonium carbonate (0.548 g, 3.48 mmol) is added. After stirring at rt for 48 h, the reaction mixture is concentrated and the residue obtained is purified by preparative HPLC to afford 3-[6-[4-(5-amino-pyridin-2-yl)-phenyl]-5-(4-chloro-phenyl)-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzamidine. 1H NMR (DMSO-d6, 400 MHz) δ 9.40 (br, 4H), 8.62 (m, 2H), 8.53 (s, 1H), 8.32 (s, 1H), 8.0 (d, 1H), 7.83 (m, 4H), 7.64 (d, 1H), 7.43 (m, 5H), 6.96 (d, 1H), 5.6 (br, 1H); LC-MS calculated for C29H21ClN8O (M+H+) 533.2, found 533.1.

Workup

  1. customto reach rt
  2. stirringstirred there for 30 h
  3. concentrationThe reaction mixture is then concentrated to a dry residue
  4. stirringAfter stirring at rt for 48 h
  5. concentrationthe reaction mixture is concentrated
  6. customthe residue obtained
  7. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-293a844dc03040b5945529e182403ce3
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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