Hydrochloric Acid → 5-(3-(1-(4-Amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-chloro-2-methoxy-6-methylphenyl)nicotinic acid dihydrochloride

HRID 1499834Notes

Reaction equation

HRID 1499834 reaction equation
[OH-:1].[Na+].[OH2:3].[NH2:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]2[N:11]([CH:15]([C:17]3[C:18]([O:33][CH3:34])=[C:19]([C:25]4[CH:26]=[N:27][CH:28]=[C:29]([CH:32]=4)[C:30]#N)[C:20]([CH3:24])=[C:21]([Cl:23])[CH:22]=3)[CH3:16])[N:12]=[C:13]([CH3:14])[C:6]=12.[ClH:35]>C(O)C>[ClH:23].[ClH:35].[NH2:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]2[N:11]([CH:15]([C:17]3[C:18]([O:33][CH3:34])=[C:19]([C:25]4[CH:26]=[N:27][CH:28]=[C:29]([CH:32]=4)[C:30]([OH:3])=[O:1])[C:20]([CH3:24])=[C:21]([Cl:23])[CH:22]=3)[CH3:16])[N:12]=[C:13]([CH3:14])[C:6]=12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 866777535-{3-[1-(4-Amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}nicotinonitrile

Product 1

HCID 866777545-(3-(1-(4-Amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-chloro-2-methoxy-6-methylphenyl)nicotinic acid dihydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

4.0 M Sodium hydroxide in water (0.3 mL, 1 mmol) was added to a mixture of 5-{3-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}nicotinonitrile (0.090 g, 0.21 mmol) in ethanol (1.0 mL) and the mixture was then heated at 95° C. for 6 h. At this time, conc. HCl was added to adjust PH to ˜3. The solvent was removed and the residue was used in the next step without further purification LCMS calculated for C22H22ClN6O3 (M+H)+: m/z=453.1; Found: 453.2.

Workup

  1. customThe solvent was removed
  2. customthe residue was used in the next step without further purification LCMS

Sources & evidence

ORD record
ord-e296cd9e31fc4c8d9c928b22d8633d9c
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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