Hydrochloric Acid → (6-Fluoro-benzothiazol-2-yl)-(R)-1-pyrrolidin-3-ylmethyl-amine, hydrochloride

HRID 222414Notes

Reaction equation

HRID 222414 reaction equation
[Cl:1]C1C=CC2N=C(NCC3CCNC3)OC=2C=1.Cl.C(OC([N:26]1[CH2:30][CH2:29][C@@H:28]([CH2:31][NH2:32])[CH2:27]1)=O)(C)(C)C.Cl[C:34]1[S:35][C:36]2[CH:42]=[C:41]([F:43])[CH:40]=[CH:39][C:37]=2[N:38]=1>O1CCOCC1>[ClH:1].[F:43][C:41]1[CH:40]=[CH:39][C:37]2[N:38]=[C:34]([NH:32][CH2:31][C@@H:28]3[CH2:29][CH2:30][NH:26][CH2:27]3)[S:35][C:36]=2[CH:42]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 1514454tert-Butyl (3S)-3-(aminomethyl)pyrrolidine-1-carboxylateHCID 20498702-Chloro-6-fluorobenzothiazoleHCID 59178006(6-Chloro-benzooxazol-2-yl)-pyrrolidin-3-ylmethyl-amine

Product 1

HCID 131728779(6-Fluoro-benzothiazol-2-yl)-(R)-1-pyrrolidin-3-ylmethyl-amine, hydrochloride

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-chloro-6-fluoro-benzothiazole (commercially available) and subsequent cleavage of the tert-butyloxy carbonyl-protecting group through treatment with HCl in dioxane. MS (m/e): 252.1 (MH+).

Sources & evidence

ORD record
ord-4221ff606a8a4a91a2a2718d083b0cfa
Source dataset
uspto-grants-2012_06
Patent number
US08207220B2

Reaction notes

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