Hydrochloric Acid → HCID 11564772, compound

HRID 2405973Notes

Reaction equation

HRID 2405973 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[CH:22]=[CH:21][NH:20][C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:10][CH2:9]1)(C)(C)C.Cl>C(OCC)C>[N:17]1[C:16]2[NH:20][CH:21]=[CH:22][C:15]=2[C:14]([N:11]2[CH2:10][CH2:9][CH:8]([NH2:7])[CH2:13][CH2:12]2)=[N:19][CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 24828975HCID 24828975, compound

Product 1

HCID 11564772HCID 11564772, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To [1-(7H-Pyrrolo[2,3-d]pyrimidin-4-yl)-piperidin-4-yl]-carbamic acid tert-butyl ester (57 mg, 0.18 mmol) was added HCl (1 ml, 4M solution in dioxane, 4 mmol). The solution was stirred at room temperature for 1 hour, and then diethyl ether was added (4 ml). The ethereal layer was discarded and the solid triturated with a further portion of ether (4 ml) and dried [product mass 27 mg]. A portion of the product was dissolved in methanol, absorbed onto an acidic resin SCX-2 cartridge, and the free base was eluted with 1M ammonia in methanol. LC/MS (LCT) Rt 0.81 [M+H]+ 218

Workup

  1. customthe solid triturated with a further portion of ether (4 ml)
  2. customdried [product mass 27 mg]
  3. dissolutionA portion of the product was dissolved in methanol
  4. customabsorbed onto an acidic resin SCX-2 cartridge
  5. washthe free base was eluted with 1M ammonia in methanol

Sources & evidence

ORD record
ord-8b6acda274a34365b43f46a228ad4b1c
Source dataset
uspto-grants-2014_08
Patent number
US08809336B2

Reaction notes

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