Hydrochloric Acid → N-[(3R)-1-(Aminoacetyl)piperidin-3-yl]-6-pyrazolo[1,5-a]pyridin-3-ylpyrazin-2-amine

HRID 1500783Notes

Reaction equation

HRID 1500783 reaction equation
Cl.[O:2]=[C:3]([N:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]([NH:19][C:20]2[CH:25]=[N:24][CH:23]=[C:22]([C:26]3[CH:27]=[N:28][N:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=34)[N:21]=2)[CH2:14]1)[CH2:4][NH:5]C(=O)OC(C)(C)C>O1CCOCC1.CO>[NH2:5][CH2:4][C:3]([N:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]([NH:19][C:20]2[CH:25]=[N:24][CH:23]=[C:22]([C:26]3[CH:27]=[N:28][N:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=34)[N:21]=2)[CH2:14]1)=[O:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86691788Tert-Butyl (2-oxo-2-{(3R)-3-[(6-pyrazolo[1,5-a]pyridin-3-ylpyrazin-2-yl)amino]piperidin-1-yl}ethyl)carbamate

Product 1

HCID 53373775N-[(3R)-1-(Aminoacetyl)piperidin-3-yl]-6-pyrazolo[1,5-a]pyridin-3-ylpyrazin-2-amineYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of hydrochloric acid in dioxane (4M, 10 mL) was added to a solution of tert-butyl (2-oxo-2-{(3R)-3-[(6-pyrazolo[1,5-a]pyridin-3-ylpyrazin-2-yl)amino]piperidin-1-yl}ethyl)carbamate (Preparation 38, 88 mg, 0.23 mmol) in methanol (3 mL) and the resulting mixture was stirred at ambient temperature for one hour. The solvents were then evaporated to half of their volume and the yellow solid that precipitated was filtered, washed with diethyl ether and dried to give the title compound (76 mg, 95%).

Workup

  1. customThe solvents were then evaporated to half of their volume
  2. customthe yellow solid that precipitated
  3. filtrationwas filtered
  4. washwashed with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-2b61ceb6c94345158ab34b14284a0367
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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