1,2,3,4-Tetrahydro-1-naphthylamine → N1-((1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(2-phenoxyethyl)amino]propyl}-5-methyl-N3,N3-dipropylisophthalamide

HRID 1783206Notes

Reaction equation

HRID 1783206 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.C1(N)[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]([CH2:51]C)[CH:50]=1)C(O)=O)=[O:41])[CH2:37][CH3:38]>>[F:8][C:6]1[CH:5]=[C:4]([CH:3]=[C:2]([F:1])[CH:7]=1)[CH2:9][C@H:10]([NH:14][C:15](=[O:24])[C:44]1[CH:48]=[C:49]([CH3:51])[CH:50]=[C:42]([C:40]([N:39]([CH2:36][CH2:37][CH3:38])[CH2:53][CH2:54][CH3:55])=[O:41])[CH:43]=1)[C@H:11]([OH:12])[CH2:13][NH:14][CH2:10][CH2:11][O:12][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=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 68609949N1-((1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(2-phenoxyethyl)amino]propyl}-5-methyl-N3,N3-dipropylisophthalamide

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—CH2—O-phenyl (VI) and “5-Me-PHTH” (IX), the title compound is obtained, MH+=582.

Sources & evidence

ORD record
ord-d80d320358b34e2787f75677ac3ae9f2
Source dataset
uspto-grants-2009_03
Patent number
US07498436B2

Reaction notes

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