(6-Chlorobenzo[1,3]dioxol-5-ylmethyl)cyclopropylamine → (rac.)-(1R*,5S*)-3-Acetyl-7-{4-[2-(2-chloro-5-fluorophenoxy)ethoxy]phenyl}-3,9-diazabicyclo[3.3.1]non-6-ene-6-carboxylic acid (6-chlorobenzo[1,3]-dioxol-5-ylmethyl)cyclopropylamide formate salt

HRID 33076Notes

Reaction equation

HRID 33076 reaction equation
ClC(Cl)(Cl)C([O:6][C:7]([N:9]1[CH:14]2[C:15]([C:36](O)=[O:37])=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][O:27][C:28]4[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=4[Cl:35])=[CH:20][CH:19]=3)[CH2:17][CH:10]1[CH2:11][N:12]([C:39](=[O:41])[CH3:40])[CH2:13]2)=[O:8])(C)C.[Cl:44][C:45]1[C:46]([CH2:54][NH:55][CH:56]2[CH2:58][CH2:57]2)=[CH:47][C:48]2[O:52][CH2:51][O:50][C:49]=2[CH:53]=1>>[CH:7]([OH:8])=[O:6].[Cl:44][C:45]1[C:46]([CH2:54][N:55]([CH:56]2[CH2:57][CH2:58]2)[C:36]([C:15]2[C@@H:14]3[NH:9][C@H:10]([CH2:17][C:16]=2[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][O:27][C:28]4[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=4[Cl:35])=[CH:20][CH:19]=2)[CH2:11][N:12]([C:39](=[O:41])[CH3:40])[CH2:13]3)=[O:37])=[CH:47][C:48]2[O:52][CH2:51][O:50][C:49]=2[CH:53]=1

Participants

3

Reactant 2

HCID 67419247(6-Chlorobenzo[1,3]dioxol-5-ylmethyl)cyclopropylamineHCID 674207933-Acetyl-7-{4-[2-(2-chloro-5-fluorophenoxy)ethoxy]phenyl}-3,9-diazabicyclo-[3.3.1]non-6-ene-6,9-dicarboxylic acid 9-(2,2,2-trichloro-1,1-dimethylethyl) ester

Product 1

HCID 131727073(rac.)-(1R*,5S*)-3-Acetyl-7-{4-[2-(2-chloro-5-fluorophenoxy)ethoxy]phenyl}-3,9-diazabicyclo[3.3.1]non-6-ene-6-carboxylic acid (6-chlorobenzo[1,3]-dioxol-5-ylmethyl)cyclopropylamide formate salt

Procedure

Synthesized according to typical procedures H and E from bicyclononene BN10 and (6-chlorobenzo[1,3]dioxol-5-ylmethyl)cyclopropylamine. LC-MS: Rt=0.90; ES+: 684.19.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-912cb49b0d2d41ffa21c8e1383418daa
Source dataset
uspto-grants-2008_09
Patent number
US07427613B2

Reaction notes

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