Hydrochloric Acid → HCID 57899420, compound

HRID 1024631Notes

Reaction equation

HRID 1024631 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[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)=[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[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)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 517111Ammonium CarbonateHCID 57899426HCID 57899426, compound

Product 1

HCID 57899420HCID 57899420, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 3-[2-[4-(5-amino-pyridin-2-yl)-phenyl]-1-(4-chloro-phenyl)-6-oxo-1,6-dihydro-purin-9-yl]-benzonitrile (prepared as described in example 43, 0.29 g, 0.56 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 (0.520 g, 3.37 mmol) is added. After stirring at rt for 24 h, the reaction mixture is concentrated and the residue obtained is purified by column chromatography to afford 3-[2-[4-(5-amino-pyridin-2-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), 8.29 (s, 1H), 8.14 (s, 1H), 7.96-8.03 (m, 3H), 7.77 (d, 2H), 7.69 (m, 1H), 7.63 (m, 2H), 7.34-7.43 (m, 5H), 6.96 (br, 1H), 5.60 (br, 2H); LC-MS calculated for C29H21ClN8O (M+H+) 533.2, found 534.2.

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 column chromatography

Sources & evidence

ORD record
ord-f231a53ff2944401a24730bc55703105
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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