2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride → HCID 67010442, compound

HRID 1630298Notes

Reaction equation

HRID 1630298 reaction equation
Cl.N1([CH2:7][C:8](O)=O)C=NC=N1.[N:11]1([CH2:16][C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25](OCC3C=CC=CC=3)=O)[CH2:21][C@H:20]2[C:35](=[O:51])[NH:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][C:44]3[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=3)=[CH:39][CH:38]=2)=[O:18])[CH:15]=[N:14][CH:13]=[N:12]1>>[N:11]1([CH2:16][C:17]([N:19]2[CH2:24][CH2:23][N:22]([CH2:25][C:8]3[CH:7]=[CH:39][CH:38]=[CH:37][CH:42]=3)[CH2:21][C@H:20]2[C:35]([NH:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][C:44]3[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=3)=[CH:39][CH:38]=2)=[O:51])=[O:18])[CH:15]=[N:14][CH:13]=[N:12]1

Participants

3

Reactant 2

HCID 448870502-(1H-1,2,4-triazol-1-yl)acetic acid hydrochlorideHCID 86659492HCID 86659492, compound

Product 1

HCID 67010442HCID 67010442, compoundYield 19%

Procedure

Proceeding as in Examples 11 and 12, but substituting 2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride and (S)-benzyl 4-(2-(1H-1,2,4-triazol-1-yl)acetyl)-3-(4-(4-fluorophenoxy)phenylcarbamoyl)piperazine-1-carboxylate, respectively, gave Compound 261, (S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)piperazine-2-carboxamide (67.9 mg, 19%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.83 (s, 1H), 8.45 (s, 1H), 7.96 (s, 1H), 7.51 (d, 2H), 7.28-7.13 (m, 7H), 7.06-6.98 (m, 4H), 5.49 (d, 1H), 5.28 (d, 1H), 4.91-4.89 (m, 1H), 3.68-3.38 (m, 5H), 2.92-2.85 (m, 1H), 2.25-2.17 (m, 2H). MS (EI) for C28H27FN6O3. found 515.3 (MH+).

Sources & evidence

ORD record
ord-4c0ece45aa894710b3bf83feaefbd4a3
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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