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1,4-Dioxane hydrochloride → (R)-1-[3-(2,3-Dihydro-benzofuran-5-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-pyrrolidin-3-ylamine

HRID 15993
Notes
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Reaction equation

HRID 15993 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13]2[N:14]=[C:15]3[N:21]([CH2:22][C:23]4[CH:24]=[CH:25][C:26]5[O:30][CH2:29][CH2:28][C:27]=5[CH:31]=4)[N:20]=[N:19][C:16]3=[N:17][CH:18]=2)[CH2:9]1)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[O:30]1[C:26]2[CH:25]=[CH:24][C:23]([CH2:22][N:21]3[C:15]4[C:16](=[N:17][CH:18]=[C:13]([N:10]5[CH2:11][CH2:12][C@@H:8]([NH2:7])[CH2:9]5)[N:14]=4)[N:19]=[N:20]3)=[CH:31][C:27]=2[CH2:28][CH2:29]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59341866{(R)-1-[3-(2,3-Dihydro-benzofuran-5-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester

Product 1

HCID 59341805(R)-1-[3-(2,3-Dihydro-benzofuran-5-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-pyrrolidin-3-ylamineYield 120.5%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

To a solution of {(R)-1-[3-(2,3-Dihydro-benzofuran-5-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-pyrrolidin-3-yl}-carbamic acid tert-butyl ester (67 mg, 0.15 mmol) in CH2Cl2 (10 mL) was added 4M HCl/Dioxane dropwise (2 mL). The reaction was stirred at room temperature for 2 hours. The organic layer was decanted and the crude solid was purified with a reverse-phased preparative HPLC eluting with acetonitrile-water having 0.1% acetic acid to provide 61 mg of (R)-1-[3-(2,3-Dihydro-benzofuran-5-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-pyrrolidin-3-ylamine as the acetate salt (99% yield).

Workup

  1. customThe organic layer was decanted
  2. customthe crude solid was purified with a reverse-phased preparative HPLC
  3. washeluting with acetonitrile-water having 0.1% acetic acid

Sources & evidence

ORD record
ord-c93b39c07aab445d82af0196f9049419
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07732604B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes