Hydrochloric Acid → HCID 86677691, compound

HRID 1499760Notes

Reaction equation

HRID 1499760 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:13]([C:15]3[C:16]([O:34][CH2:35][CH3:36])=[C:17]([C:23]4[CH:24]=[CH:25][C:26]([C:29]([N:31]([CH3:33])[CH3:32])=[O:30])=[N:27][CH:28]=4)[C:18]([CH3:22])=[C:19]([Cl:21])[CH:20]=3)[CH3:14])[N:9]=[C:10]([CH:11]=[CH2:12])[C:3]=12.Cl.O>[Pt].CO>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:13]([C:15]3[C:16]([O:34][CH2:35][CH3:36])=[C:17]([C:23]4[CH:24]=[CH:25][C:26]([C:29]([N:31]([CH3:33])[CH3:32])=[O:30])=[N:27][CH:28]=4)[C:18]([CH3:22])=[C:19]([Cl:21])[CH:20]=3)[CH3:14])[N:9]=[C:10]([CH2:11][CH3:12])[C:3]=12

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86677690HCID 86677690, compound

Product 1

HCID 86677691HCID 86677691, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

5-{3-[1-(4-Amino-3-vinyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-ethoxy-6-methylphenyl}-N,N-dimethylpyridine-2-carboxamide (14 mg, 0.028 mmol) and 5% platinum on carbon (14 mg) was combined in methanol (1 mL), to which was added 0.25 M hydrogen chloride in water (0.28 mL, 0.069 mmol). The suspension was hydrogenated under balloon pressure of H2 at room temperature for 3 h. The suspension was filtered and the filtrate purified on RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min) to give the desired product (3.9 mg, 28%). The product was isolated as a racemic mixture. LCMS calculated for C26H31ClN7O2(M+H)+: m/z=508.2; Found: 508.3.

Workup

  1. filtrationThe suspension was filtered
  2. customthe filtrate purified on RP-HPLC (XBridge C18 column
  3. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-202b1064a1994b6c88f971a03d294b62
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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