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

HRID 1350945Notes

Reaction equation

HRID 1350945 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:14][C:15](=[O:21])OC(C)(C)C)[C@H:11]2[CH2:13][O:12]2)[CH:5]=[C:6]([F:8])[CH:7]=1.[CH:22]1([NH2:32])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][CH2:23]1.[CH2:33]([N:36]([CH2:50][CH2:51][CH3:52])[C:37]([C:39]1[CH:40]=[C:41]([CH:45]=[C:46]([CH2:48]C)[CH:47]=1)C(O)=O)=[O:38])[CH2:34][CH3:35]>>[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:21])[C:41]1[CH:45]=[C:46]([CH3:48])[CH:47]=[C:39]([C:37]([N:36]([CH2:33][CH2:34][CH3:35])[CH2:50][CH2:51][CH3:52])=[O:38])[CH:40]=1)[C@H:11]([OH:12])[CH2:13][NH:32][C@H:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 3

HCID 180661,2,3,4-Tetrahydro-1-naphthylamineHCID 9922319tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamateHCID 225936423-[(Dipropylamino)carbonyl]-5-Ethylbenzoic Acid

Product 1

HCID 69417358N1-{(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(1R)-1,2,3,4-tetrahydro-1-naphthalenylamino]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, EXAMPLE 3), 1,2,3,4-tetrahydro-1-naphthalenylamine (VI) and “5-Me-PHTH” (IX), the title compound is obtained, MH+=588.

Sources & evidence

ORD record
ord-564ab25154bb44a09458deb31ffcaeb5
Source dataset
uspto-grants-2007_05
Patent number
US07214715B2

Reaction notes

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