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

HRID 1783207Notes

Reaction equation

HRID 1783207 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]([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:35][CH2:25][C:34]1[CH:29]=[CH:30][CH:31]=[C:32]([O:41][CH2:40][CH:42]([CH3:43])[CH3:50])[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 69413411N1-{(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(3-isobutoxybenzyl)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-phenyl-O-i-butyl (VI) and “5-Me-PHTH” (IX), the title compound is obtained, MH+=624.

Sources & evidence

ORD record
ord-d0513e3bdf4b4036a27a41877ea30055
Source dataset
uspto-grants-2009_03
Patent number
US07498436B2

Reaction notes

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