[2-(S)-(2-(R)-Methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone → {4-[5-(Azetidine-1-carbonyl)-thiophen-2-yl]-phenyl}-[2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-methanone

HRID 646439Notes

Reaction equation

HRID 646439 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13]([C:15]1[CH:20]=[CH:19][C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][CH:16]=1)=[O:14].[N:30]1([C:34]([C:36]2[S:37][C:38](Br)=[CH:39][CH:40]=2)=[O:35])[CH2:33][CH2:32][CH2:31]1>>[N:30]1([C:34]([C:36]2[S:37][C:38]([C:18]3[CH:19]=[CH:20][C:15]([C:13]([N:9]4[CH2:10][CH2:11][CH2:12][C@H:8]4[CH2:7][N:3]4[CH2:4][CH2:5][CH2:6][C@H:2]4[CH3:1])=[O:14])=[CH:16][CH:17]=3)=[CH:39][CH:40]=2)=[O:35])[CH2:33][CH2:32][CH2:31]1

Participants

3

Reactant 2

HCID 57980025[2-(S)-(2-(R)-Methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanoneHCID 59264666Azetidin-1-yl(5-bromothiophen-2-yl)methanone

Product 1

HCID 11647806{4-[5-(Azetidine-1-carbonyl)-thiophen-2-yl]-phenyl}-[2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-methanoneYield 21%

Procedure

The title compound is prepared in a manner substantially analogous to General Procedure A using [2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone (367 mg, 0.92 mmol) and azetidin-1-yl-(5-bromo-thiophen-2-yl)-methanone) (226 mg, 0.92 mmol) to give 80 mg (21% yield). MS (ES+) 438.3 (M+H)+

Workup

  1. customto give 80 mg (21% yield)

Sources & evidence

ORD record
ord-bd52589dbeb640278a13d01fd54c996c
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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