n-[2-Chloro-5-(2-methoxyethyl)benzyl]cyclopropanamine → (rac.)-(1R*,5S*)-6-{[2-Chloro-5-(2-methoxy-ethyl)-benzyl]-cyclopropyl-carbamoyl}-7-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethyl]-phenyl}-3,9-diaza-bicyclo[3.3.1]non-6-ene

HRID 2428208Notes

Reaction equation

HRID 2428208 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]([CH2:33][CH2:34][O:35][C:36]4[C:41]([Cl:42])=[CH:40][C:39]([CH3:43])=[CH:38][C:37]=4[Cl:44])=[CH:29][CH:28]=3)=[C:13]2[C:24](O)=[O:25])[CH2:9]1)=O)(C)(C)C.[Cl:45][C:46]1[CH:56]=[CH:55][C:54]([CH2:57][CH2:58][O:59][CH3:60])=[CH:53][C:47]=1[CH2:48][NH:49][CH:50]1[CH2:52][CH2:51]1>>[Cl:45][C:46]1[CH:56]=[CH:55][C:54]([CH2:57][CH2:58][O:59][CH3:60])=[CH:53][C:47]=1[CH2:48][N:49]([CH:50]1[CH2:51][CH2:52]1)[C:24]([C:13]1[C@@H:14]2[NH:16][C@H:10]([CH2:11][C:12]=1[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][O:35][C:36]3[C:41]([Cl:42])=[CH:40][C:39]([CH3:43])=[CH:38][C:37]=3[Cl:44])=[CH:29][CH:28]=1)[CH2:9][NH:8][CH2:15]2)=[O:25]

Participants

3

Reactant 2

HCID 51350448n-[2-Chloro-5-(2-methoxyethyl)benzyl]cyclopropanamineHCID 131728992(rac.)-(1R*,5S*)-7-{4-[2-(2,6-Dichloro-4-methyl-phenoxy)-ethyl]-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 67479308(rac.)-(1R*,5S*)-6-{[2-Chloro-5-(2-methoxy-ethyl)-benzyl]-cyclopropyl-carbamoyl}-7-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethyl]-phenyl}-3,9-diaza-bicyclo[3.3.1]non-6-ene

Procedure

From (rac.)-(1R*,5S*)-7-{4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethyl]-phenyl}-3,9-diaza-bicyclo[3.3.1]non-6-ene-3,6,9-tricarboxylic acid 3,9-di-tert-butyl ester, as for compound L1, but using N-[2-chloro-5-(2-methoxyethyl)benzyl]cyclopropanamine instead of N-[2-chloro-5-(3-methoxypropyl)benzyl]cyclopropanamine, then as for Example 1, the desired compound was obtained. MS (M+1) ESI 668.

Sources & evidence

ORD record
ord-eb93740b652c42828e3d634d149ecb8f
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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