Hydrochloric Acid → 5-(1-(6-(1,4-diazepan-1-yl)pyridin-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-methylpyrazin-2-amine

HRID 57913Notes

Reaction equation

HRID 57913 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:9]2[N:14]=[CH:13][C:12]3[CH:15]=[N:16][N:17]([C:18]4[N:23]=[C:22]([N:24]5[CH2:30][CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]5)[CH:21]=[CH:20][CH:19]=4)[C:11]=3[CH:10]=2)=[N:6][C:7]=1[CH3:8].Cl>CO.O1CCOCC1>[N:24]1([C:22]2[N:23]=[C:18]([N:17]3[C:11]4[CH:10]=[C:9]([C:5]5[N:6]=[C:7]([CH3:8])[C:2]([NH2:1])=[N:3][CH:4]=5)[N:14]=[CH:13][C:12]=4[CH:15]=[N:16]3)[CH:19]=[CH:20][CH:21]=2)[CH2:30][CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86707104Tert-butyl 4-[6-[6-(5-amino-6-methyl-pyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-1,4-diazepane-1-carboxylate

Product 1

HCID 727143845-(1-(6-(1,4-diazepan-1-yl)pyridin-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-methylpyrazin-2-amineYield 4.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-[6-[6-(5-amino-6-methyl-pyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-1,4-diazepane-1-carboxylate (0.2293 mmol; 115 mg) in Methanol (10 mL) was added hydrochloric acid, 4.0 M in 1,4-Dioxane (5 mL). The resulting mixture was stirred at room temperature overnight. The mixture was concentrated and the residue was purified by reverse phase HPLC to afford 208 as an off-white solid (4.0 mg, 4.3%). MS (ESI) m/z: 402.1 [M+H]+

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-494d52cf1bef42c79b1c307f0482524b
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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