n-[2-Chloro-5-(2-methoxyethyl)benzyl]cyclopropanamine → (1R,5S)-7-{4-[2-(2,6-Dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-3,9-diaza-bicyclo[3.3.1]non-6-ene-6-carboxylic Acid [2-chloro-5-(2-methoxy-ethyl)-benzyl]-cyclopropyl-amide

HRID 2428211Notes

Reaction equation

C(OC([N:8]1[CH2:15][C@H:14]2[N:16](C(OC(C)(C)C)=O)[C@H:10]([CH2:11][C:12]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][O:36][C:37]4[C:42]([Cl:43])=[CH:41][C:40]([CH3:44])=[CH:39][C:38]=4[Cl:45])=[CH:29][CH:28]=3)=[C:13]2[C:24](O)=[O:25])[CH2:9]1)=O)(C)(C)C.[Cl:46][C:47]1[CH:57]=[CH:56][C:55]([CH2:58][CH2:59][O:60][CH3:61])=[CH:54][C:48]=1[CH2:49][NH:50][CH:51]1[CH2:53][CH2:52]1>>[Cl:46][C:47]1[CH:57]=[CH:56][C:55]([CH2:58][CH2:59][O:60][CH3:61])=[CH:54][C:48]=1[CH2:49][N:50]([CH:51]1[CH2:52][CH2:53]1)[C:24]([C:13]1[C@@H:14]2[NH:16][C@H:10]([CH2:11][C:12]=1[C:27]1[CH:28]=[CH:29][C:30]([O:33][CH2:34][CH2:35][O:36][C:37]3[C:42]([Cl:43])=[CH:41][C:40]([CH3:44])=[CH:39][C:38]=3[Cl:45])=[CH:31][CH:32]=1)[CH2:9][NH:8][CH2:15]2)=[O:25]

Participants

Reactant 2

HCID 51350448n-[2-Chloro-5-(2-methoxyethyl)benzyl]cyclopropanamine

HCID 67149015(1R,5S)-7-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-3,9-diaza-bicyclo[3.3.1]non-6-ene-3,6,9-tricarboxylic acid 3,9-di-tert-butyl ester

Product 1

HCID 67149045(1R,5S)-7-{4-[2-(2,6-Dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-3,9-diaza-bicyclo[3.3.1]non-6-ene-6-carboxylic Acid [2-chloro-5-(2-methoxy-ethyl)-benzyl]-cyclopropyl-amide

Procedure

This compound was synthesized from (1R,5S)-7-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-phenyl}-3,9-diaza-bicyclo[3.3.1]non-6-ene-3,6,9-tricarboxylic acid 3,9-di-tert-butyl ester and [2-chloro-5-(2-methoxy-ethyl)-benzyl]-cyclopropyl-amine as for compound L1, and then Example 1. MS (ESI, Q+) m/z 686.1.

Sources & evidence

ORD record: ord-4686f2c4d7304475aec84d235cb7977c
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968720B2

Reaction notes

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