HCID 60139827, compound → HCID 60139851, compound

HRID 883112Notes

Reaction equation

HRID 883112 reaction equation
N(CCC[C@@]1(C2C=CC=CC=2)N(C(=O)[C@@H](O[Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)C)N=C(C2C=C(F)C=CC=2F)S1)=[N+]=[N-].[NH2:48][CH2:49][CH2:50][CH2:51][C@:52]1([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[N:56]([C:57](=[O:62])[C@@H:58]([O:60][CH3:61])[CH3:59])[N:55]=[C:54]([C:63]2[CH:68]=[C:67]([F:69])[CH:66]=[CH:65][C:64]=2[F:70])[S:53]1>>[NH2:48][CH2:49][CH2:50][CH2:51][C@@:52]1([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[N:56]([C:57](=[O:62])[C@@H:58]([O:60][CH3:61])[CH3:59])[N:55]=[C:54]([C:63]2[CH:68]=[C:67]([F:69])[CH:66]=[CH:65][C:64]=2[F:70])[S:53]1

Participants

3

Reactant 2

HCID 60139827HCID 60139827, compoundHCID 86604836HCID 86604836, compound

Product 1

HCID 60139851HCID 60139851, compound

Procedure

Prepared as previously described in Example 71 using (S)-1-((R)-2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2-(tert-butyldiphenylsilyloxy)propan-1-one from Step C. MS ESI (+) m/z 420 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 7.51 (m, 1H), 7.44 (m, 2H), 7.36 (m, 2H), 7.29 (m, 1H), 7.12 (m, 2H), 4.71 (q, 1H, J=6 Hz), 3.32 (s, 3H), 3.23 (m, 1H), 2.84 (m, 2H), 2.43 (m, 1H), 1.93 (m, 1H), 1.50 (d, 3H, J=6 Hz), 1.44 (m, 2H), 1.34 (m, 1H). Stereochemistry was assigned by inference from (S)-1-((S)-2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2-methoxypropan-1-one.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-03c2f7823616422e9285e1428a894a9c
Source dataset
uspto-grants-2012_08
Patent number
US08236825B2

Reaction notes

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