HCID 11404194, compound → HCID 60139851, compound

HRID 2189933Notes

Reaction equation

HRID 2189933 reaction equation
[Si](OC(C)C=O)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2:23][CH2:24][CH2:25][CH2:26][C@:27]1([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[N:31]([C:32](=[O:37])[C@@H:33]([O:35][CH3:36])[CH3:34])[N:30]=[C:29]([C:38]2[CH:43]=[C:42]([F:44])[CH:41]=[CH:40][C:39]=2[F:45])[S:28]1>>[NH2:23][CH2:24][CH2:25][CH2:26][C@@:27]1([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[N:31]([C:32](=[O:37])[C@@H:33]([O:35][CH3:36])[CH3:34])[N:30]=[C:29]([C:38]2[CH:43]=[C:42]([F:44])[CH:41]=[CH:40][C:39]=2[F:45])[S:28]1

Participants

3

Reactant 2

HCID 11404194HCID 11404194, compoundHCID 60139827HCID 60139827, compound

Product 1

HCID 60139851HCID 60139851, compound

Procedure

Prepared as described in Example 5. Steps A-G, using (S)-1-((R)-2-(3-azidopropyl)-5-(2,5-difluorophenyl)-1)-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-7be311f8bcef47c18dfc8c1a77c2321f
Source dataset
uspto-grants-2012_12
Patent number
US08324257B2

Reaction notes

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