HCID 15286443, compound → HCID 60139783, compound

HRID 883114Notes

Reaction equation

[Si](O[C@H](C)C(O)=O)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2:24][CH2:25][CH2:26][CH2:27][C@:28]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[N:32]([C:33](=[O:38])[C@@H:34]([O:36][CH3:37])[CH3:35])[N:31]=[C:30]([C:39]2[CH:44]=[C:43]([F:45])[CH:42]=[CH:41][C:40]=2[F:46])[S:29]1.NCCC[C@@]1(C2C=CC=CC=2)N(C(=O)[C@@H](OC)C)N=C(C2C=C(F)C=CC=2F)S1>>[NH2:24][CH2:25][CH2:26][CH2:27][C@:28]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[N:32]([C:33](=[O:38])[C@H:34]([O:36][CH3:37])[CH3:35])[N:31]=[C:30]([C:39]2[CH:44]=[C:43]([F:45])[CH:42]=[CH:41][C:40]=2[F:46])[S:29]1

Participants

Reactant 3

HCID 15286443HCID 15286443, compound

HCID 60139827HCID 60139827, compound

HCID 60139851HCID 60139851, compound

Product 1

HCID 60139783HCID 60139783, compound

Procedure

Prepared as previously described in Example 71 using (R)-2-(t-butyldiphenylsilyloxy)propanoic acid in place of (S)-2-(t-butyldiphenylsilyloxy)propanoic acid. MS ESI (+) m/z 420 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 7.52 (m, 1H), 7.46 (d, 2H, J=7 Hz), 7.37 (t, 2H, J=8 Hz), 7.30 (t, 1H, J=7 Hz), 7.13 (m, 2H), 4.71 (q, 1H, J=6 Hz), 3.32 (s, 3H), 3.24 (m, 1H), 2.83 (m, 2H), 2.43 (m, 1H), 1.92 (m, 1H), 1.51 (d, 3H, J=6 Hz), 1.45 (m, 1H). Stereochemistry was assigned by comparison to (S)-1-((S)-2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2-methoxypropan-1-one and (S)-1-((R)-2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2-methoxypropan-1-one.

Workup

customPrepared

Sources & evidence

ORD record: ord-de857a8d1d5b456388492e2c948c6086
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236825B2

Reaction notes

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