Hydrochloric Acid → HCID 25122894, compound

HRID 1931637Notes

Reaction equation

HRID 1931637 reaction equation
[ClH:1].[CH:2]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([O:23][C:24]4[C:25]([CH3:30])=[N:26][CH:27]=[CH:28][CH:29]=4)=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3]>CCOCC>[ClH:1].[CH:2]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:18]3=[N:19][CH:20]=[N:21][C:22]([O:23][C:24]4[C:25]([CH3:30])=[N:26][CH:27]=[CH:28][CH:29]=4)=[C:17]3[CH:16]=[N:15]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 25122895HCID 25122895, compound

Product 1

HCID 25122894HCID 25122894, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

HCl (Sigma Aldrich Chemical Company, Inc., Milwaukee, Wis., USA 2M in ether; 0.43 mL, 0.86 mmol) was added to a solution of 4-[4-(2-Methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid isopropyl ester (170 mg, 0.43 mmol) in anhydrous ether (2 mL). The resulting mixture was shaken at room temperature for 10 min. The solvent was evaporated under high vacuum to give a white powder which still contained some ether by NMR. The solid was ground to a fine powder using a spatula and then it was held overnight in a vacuum oven overnight at 80° C. to give 4-[4-(2-methyl-pyridin-3-yloxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid isopropyl ester hydrochloride salt (147 mg, 79%) as a white powder. 1H NMR (300 MHz, CDCl3) δ 1.28 (d, 6H, J=6.0 Hz), 2.01-2.04 (m, 2H), 2.22-2.31 (m, 2H), 2.87 (s, 3H), 2.98-3.06 (m, 2H), 4.30-4.42 (m, 2H), 4.95-5.05 (m, 2H), 7.79-7.84 (m, 1H), 8.19-8.24 (m, 2H), 8.44 (s, 1H), 8.61-8.63 (m, 1H).

Workup

  1. customThe solvent was evaporated under high vacuum
  2. customto give a white powder which
  3. waitit was held overnight in a vacuum oven overnight at 80° C.

Sources & evidence

ORD record
ord-a8133f65a3904e8c98eae9f2dbccf3b8
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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