Hydrochloric Acid → (6-Chloro-quinoxalin-2-yl)-(R)-1-pyrrolidin-3-ylmethyl-amine

HRID 403334

Reaction equation

HRID 403334 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([NH:9][CH2:10][CH:11]3[CH2:15][CH2:14][NH:13][CH2:12]3)O[C:4]=2[CH:3]=1.Cl.C(O[C:24]([N:26]1CC[C@@H](CN)C1)=O)(C)(C)C.ClC1C=NC2C(=CC=C(Cl)C=2)N=1>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:16][CH:17]=1)[N:6]=[C:7]([NH:9][CH2:10][C@@H:11]1[CH2:15][CH2:14][NH:13][CH2:12]1)[CH:24]=[N:26]2

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 877482,6-DichloroquinoxalineHCID 1514454tert-Butyl (3S)-3-(aminomethyl)pyrrolidine-1-carboxylateHCID 59178006(6-Chloro-benzooxazol-2-yl)-pyrrolidin-3-ylmethyl-amine

Product 1

HCID 58200843(6-Chloro-quinoxalin-2-yl)-(R)-1-pyrrolidin-3-ylmethyl-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In analogy to the procedure described for the synthesis of (6-Chloro-benzooxazol-2-yl)-pyrrolidin-3-ylmethyl-amine; hydrochloride (example 1, step 2) the title compound was prepared from (S)-3-aminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester and 2,6-dichloro-quinoxaline (commercially available) and subsequent cleavage of the tert-butyloxy carbonyl-protecting group through treatment with HCl in dioxane. MS (m/e): 263.1 (MH+).

Sources & evidence

ORD record
ord-779eab3f4ffd4be68209f1a6b665f8a8
Source dataset
uspto-grants-2014_06
Patent number
US08748430B2

Linked notes

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