HCID 60139827, compound → HCID 60139802, compound

HRID 883115Notes

Reaction equation

[N:1]([CH2:4][CH2:5][CH2:6][C@@:7]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:11]([C:12](=[O:17])[C@H:13]([O:15][CH3:16])[CH3:14])[N:10]=[C:9]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])[S:8]1)=[N+]=[N-].NCCC[C@]1(C2C=CC=CC=2)N(C(=O)[C@@H](OC)C)N=C(C2C=C(F)C=CC=2F)S1.NCCC[C@@]1(C2C=CC=CC=2)N(C(=O)[C@@H](OC)C)N=C(C2C=C(F)C=CC=2F)S1>>[NH2:1][CH2:4][CH2:5][CH2:6][C@@:7]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:11]([C:12](=[O:17])[C@H:13]([O:15][CH3:16])[CH3:14])[N:10]=[C:9]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])[S:8]1

Participants

Reactant 3

HCID 60139827HCID 60139827, compound

HCID 60139851HCID 60139851, compound

HCID 86604837HCID 86604837, compound

Product 1

HCID 60139802HCID 60139802, compound

Procedure

Prepared as previously described in Example 75 using (R)-1-((R)-2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2-methoxypropan-1-one. MS ESI (+) m/z 420 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 7.52 (m, 1H), 7.44 (d, 2H, J=7 Hz), 7.35 (t, 2H, J=8 Hz), 7.29 (t, 1H, J=7 Hz), 7.13 (m, 2H), 4.68 (q, 1H, J=6 Hz), 3.41 (s, 3H), 3.24 (m, 1H), 2.85 (m, 2H), 2.43 (m, 1H), 1.95 (m, 1H), 1.54 (br, 3H), 1.46 (d, 3H, J=6 Hz). 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-5f3526e0e650479ea4695959ab0c5e4a
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236825B2

Reaction notes

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