(3R)-3-fluoropyrrolidine hydrochloride → (R)-1-(4-Fluorophenyl)-6-[5-((R)-3-fluoropyrrolidin-1-yl)-pyridine-3-sulfonyl]-4a-methoxymethyl-4,4a,5,6,7,8-hexahydro-1H-1,2,6-triaza-cyclopenta[b]naphthalene

HRID 1907304Notes

Reaction equation

HRID 1907304 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:8]([N:11]2[CH2:20][CH2:19][C:18]3[C@:13]([CH2:31][O:32][CH3:33])([CH2:14][C:15]4[CH:23]=[N:22][N:21]([C:24]5[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=5)[C:16]=4[CH:17]=3)[CH2:12]2)(=[O:10])=[O:9])[CH:5]=[N:6][CH:7]=1.Cl.[F:35][C@@H:36]1[CH2:40][CH2:39][NH:38][CH2:37]1>>[F:30][C:27]1[CH:28]=[CH:29][C:24]([N:21]2[C:16]3[CH:17]=[C:18]4[C@:13]([CH2:31][O:32][CH3:33])([CH2:14][C:15]=3[CH:23]=[N:22]2)[CH2:12][N:11]([S:8]([C:4]2[CH:5]=[N:6][CH:7]=[C:2]([N:38]3[CH2:39][CH2:40][C@@H:36]([F:35])[CH2:37]3)[CH:3]=2)(=[O:10])=[O:9])[CH2:20][CH2:19]4)=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 2759162(3R)-3-fluoropyrrolidine hydrochlorideHCID 66779670(R)-6-(5-Bromopyridine-3-sulfonyl)-1-(4-fluorophenyl)-4a-methoxymethyl-4,4a,5,6,7,8-hexahydro-1H-1,2,6-triazacyclopenta[b]naphthalene

Product 1

HCID 66780079(R)-1-(4-Fluorophenyl)-6-[5-((R)-3-fluoropyrrolidin-1-yl)-pyridine-3-sulfonyl]-4a-methoxymethyl-4,4a,5,6,7,8-hexahydro-1H-1,2,6-triaza-cyclopenta[b]naphthalene

Procedure

The title compound was prepared by the method of Preparation 12c using (R)-6-(5-bromopyridine-3-sulfonyl)-1-(4-fluorophenyl)-4a-methoxymethyl-4,4a,5,6,7,8-hexahydro-1H-1,2,6-triazacyclopenta[b]naphthalene and (R)-3-fluoropyrrolidine hydrochloride. LCMS (Method F): 542 (M+H)+, Retention time 4.9 minutes.

Sources & evidence

ORD record
ord-8fbfeb06e36a46fe9fc91d4c7994c431
Source dataset
uspto-grants-2013_12
Patent number
US08598154B2

Reaction notes

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