1,2,3,4-Tetrahydro-1-naphthylamine → N1-[(1S,2R)-3-(benzylamino)-1-(3,5-difluorobenzyl)-2-hydroxypropyl]-N3-methyl-N3-propylisophthalamide

HRID 1350948Notes

Reaction equation

HRID 1350948 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:14][C:15](=[O:24])OCC2C=CC=CC=2)[C@H:11]2[CH2:13][O:12]2)[CH:5]=[C:6]([F:8])[CH:7]=1.[CH:25]1([NH2:35])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)CCC1.[CH2:36]([N:39]([CH2:53][CH2:54][CH3:55])[C:40]([C:42]1[CH:43]=[C:44]([CH:48]=[C:49](CC)[CH:50]=1)C(O)=O)=[O:41])CC>>[CH2:25]([NH:35][CH2:13][C@@H:11]([OH:12])[C@@H:10]([NH:14][C:15](=[O:24])[C:44]1[CH:48]=[CH:49][CH:50]=[C:42]([C:40]([N:39]([CH3:36])[CH2:53][CH2:54][CH3:55])=[O:41])[CH:43]=1)[CH2:9][C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=1)[C:34]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 3

HCID 180661,2,3,4-Tetrahydro-1-naphthylamineHCID 10131699HCID 10131699, compoundHCID 225936423-[(Dipropylamino)carbonyl]-5-Ethylbenzoic Acid

Product 1

HCID 69413593N1-[(1S,2R)-3-(benzylamino)-1-(3,5-difluorobenzyl)-2-hydroxypropyl]-N3-methyl-N3-propylisophthalamide

Procedure

Following the general procedure of EXAMPLEs 4, 5 and 6 and making non-critical variations but using tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V), H2N—CH2-phenyl (VI) and (CH3—CH2—CH2—)(CH3—)N—CO—(CH3—)phenyl-CO—OH (IX) where the attachment to the -phenyl-ring for the carbonyls is 1-,3- and 5- for the methyl group, the title compound is obtained, MH+=510.

Sources & evidence

ORD record
ord-9cae7e2f80264cd88d9f960d29cbf5ee
Source dataset
uspto-grants-2007_05
Patent number
US07214715B2

Reaction notes

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