Hydrochloric Acid → HCID 11535873, compound

HRID 1036315Notes

Reaction equation

HRID 1036315 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[CH:18][N:17]=[C:16]3[NH:20][N:21]=[CH:22][C:15]=23)[CH2:10][CH2:9]1)(C)(C)C.Cl>C(OCC)C>[NH:20]1[C:16]2=[N:17][CH:18]=[N:19][C:14]([N:11]3[CH2:12][CH2:13][CH:8]([NH2:7])[CH2:9][CH2:10]3)=[C:15]2[CH:22]=[N:21]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 24828862HCID 24828862, compound

Product 1

HCID 11535873HCID 11535873, compoundYield 177%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To [1-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)-piperidin-4-yl]-carbamic acid tert-butyl ester (28 mg, 0.088 mmol) was added HCl (1 ml, 4M solution in dioxane, 4 mmol). The suspension was stirred at room temperature for 1 hour, and then diluted with diethyl ether (4 ml). The ethereal layer was discarded and the solid washed with a further portion of diethyl ether (2 ml). The ethereal layer was again discarded, and the resultant solid dried under high vacuum to yield the desired product (34 mg). The free base was liberated by dissolution of this material in methanol, loading onto an acidic resin SCX-2 cartridge, and elution from the cartridge with ammonia in methanol. LC/MS Rt 0.86 [M+H]+ 219

Workup

  1. washthe solid washed with a further portion of diethyl ether (2 ml)
  2. customthe resultant solid dried under high vacuum

Sources & evidence

ORD record
ord-2138a1621b124ca8abff490191f3dc43
Source dataset
uspto-grants-2013_10
Patent number
US08546407B2

Reaction notes

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