Hydrochloric Acid → HCID 57899403, compound

HRID 1024640Notes

Reaction equation

HRID 1024640 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[N:18]=[CH:19][N:20]([C:23]5[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=5)[C:26]#[N:27])[C:21]=4[N:22]=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[N:18]=[CH:19][N:20]([C:23]5[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=5)[C:26]([NH2:44])=[NH:27])[C:21]=4[N:22]=3)=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 517111Ammonium CarbonateHCID 57899382HCID 57899382, compound

Product 1

HCID 57899403HCID 57899403, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 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 44, 0.30 g, 0.58 mmol), methanol saturated with hydrogen chloride gas (15 mL) is added at 0° C. with stirring. The reaction mixture is allowed to reach rt and stirred there for 12 h. The reaction mixture is then concentrated to a dry residue. It is taken in dry methanol (15 mL) and ammonium carbonate (0.540 g, 3.48 mmol) is added. After stirring at rt for 24 h, the reaction mixture is concentrated and the residue obtained is purified by preparative HPLC to afford 3-[2-[4-(6-amino-pyridin-3-yl)-phenyl]-1-(4-chloro-phenyl)-6-oxo-1,6-dihydro-purin-9-yl]-benzamidine. 1H NMR (DMSO-d6, 400 MHz) δ 8.65 (s, 1H), 8.28 (s, 1H), 8.22 (m, 1H), 8.15 (br, 2H), 7.96-8.03 (m, 2H), 7.67 (m, 2H), 7.59 (s, 1H), 7.45-7.50 (m, 9H), 6.47 (d, 1H), 6.15 (br, 1H); LC-MS calculated for C29H21ClN8O (M+H+) 533.2, found 534.0.

Workup

  1. customto reach rt
  2. stirringstirred there for 12 h
  3. concentrationThe reaction mixture is then concentrated to a dry residue
  4. stirringAfter stirring at rt for 24 h
  5. concentrationthe reaction mixture is concentrated
  6. customthe residue obtained
  7. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-907187c3c45d4d5a89f75518dda2d3c6
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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