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

HRID 1499854Notes

Reaction equation

[OH-:1].[Na+].[NH2:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]2[N:10]([CH:14]([C:16]3[C:17]([O:32][CH3:33])=[C:18]([C:24]4[CH:29]=[CH:28][N:27]=C(C#N)[CH:25]=4)[C:19]([CH3:23])=[C:20]([Cl:22])[CH:21]=3)[CH3:15])[N:11]=[C:12]([CH3:13])[C:5]=12.[ClH:34].[CH2:35]([OH:37])[CH3:36]>>[ClH:22].[ClH:34].[NH2:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]2[N:10]([CH:14]([C:16]3[C:17]([O:32][CH3:33])=[C:18]([C:24]4[CH:29]=[CH:28][N:27]=[C:36]([C:35]([OH:1])=[O:37])[CH:25]=4)[C:19]([CH3:23])=[C:20]([Cl:22])[CH:21]=3)[CH3:15])[N:11]=[C:12]([CH3:13])[C:5]=12

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 14798Sodium Hydroxide

HCID 866776424-{3-[1-(4-Amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-ethyl]-5-chloro-2-methoxy-6-methylphenyl}pyridine-2-carbonitrile

Product 1

HCID 866777774-(3-(1-(4-Amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-5-chloro-2-methoxy-6-methylphenyl)picolinic acid dihydrochloride

Conditions

Temperature: 95 °C

Procedure

1.0 M Sodium hydroxide (2.9 mL, 2.9 mmol) was added to a mixture of 4-{3-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}pyridine-2-carbonitrile (0.250 g, 0.576 mmol) in ethanol (4.0 mL) and the resulting mixture was heated at 95° C. for 6 h. At this time, conc. HCl was added to adjust the 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

customThe solvent was removed
customthe residue was used in the next step without further purification

Sources & evidence

ORD record: ord-727a26e1243f464289f3418354906f90
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199982B2

Reaction notes

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