2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride → HCID 67010766, compound

HRID 1630178Notes

Reaction equation

HRID 1630178 reaction equation
Cl.[N:2]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[N:5][CH:4]=[N:3]1.[NH2:11][C@@H:12]([CH2:30][O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[CH:18][CH:17]=1)=[O:14]>>[N:2]1([CH2:7][C:8]([NH:11][C@@H:12]([CH2:30][O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:13]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([S:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[CH:20][CH:21]=2)=[O:14])=[O:10])[CH:6]=[N:5][CH:4]=[N:3]1

Participants

3

Reactant 2

HCID 448870502-(1H-1,2,4-triazol-1-yl)acetic acid hydrochlorideHCID 67009713HCID 67009713, compound

Product 1

HCID 67010766HCID 67010766, compoundYield 18%

Procedure

Proceeding as in Example 1, but substituting 2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride and (S)-2-amino-3-(benzyloxy)-N-(4-(4-fluorophenylthio)phenyl)propanamide, gave Compound 178, (S)-2-(2-(1H-1,2,4-triazol-1-yl)acetamido)-3-(benzyloxy)-N-(4-(4-fluorophenylthio)phenyl)propanamide (100.1 mg, 18%). 1H-NMR (400 MHz, CDCl3): δ 8.57 (s, 1H), 8.19 (s, 1H), 8.03 (s, 1H), 7.38-7.21 (m, 13H), 7.03-6.96 (m, 2H), 4.92 (s, 2H), 4.73-4.67 (m, 1H), 4.61 (d, 1H), 4.52 (d, 1H), 3.97-3.91 (dd, 1H), 3.57 (t, 1H). MS (EI) for C26H25FN5O3S found 506 (MH+).

Sources & evidence

ORD record
ord-eb528a764c56463f8d9fd5fc3a07c8c9
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…