2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride → HCID 67009500, compound

HRID 1630181Notes

Reaction equation

HRID 1630181 reaction equation
Cl.[N:2]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[N:5][CH:4]=[N:3]1.[CH2:11]([C@H:18]1[CH2:22][NH:21][C@H:20]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=3)=[CH:28][CH:27]=2)=[O:24])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[N:2]1([CH2:7][C:8]([N:21]2[CH2:22][C@H:18]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:19][C@H:20]2[C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=3)=[CH:28][CH:27]=2)=[O:24])=[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 67010395HCID 67010395, compound

Product 1

HCID 67009500HCID 67009500, compoundYield 37%

Procedure

Proceeding as in Example 1, but substituting 2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-chlorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 79, (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-benzyl-N-(4-(4-chlorophenoxy)phenyl)pyrrolidine-2-carboxamide (187 mg, 37%). 1H-NMR (400 MHz, CDCl3): σ 9.04 (s, 1H), 8.24 (s, 1H), 7.99 (s, 1H), 7.43 (d, 2H), 7.31 (d, 2H), 7.27-7.18 (m, 4H), 6.93 (d, 2H), 6.88 (d, 2H), 5.03 (d, 1H), 4.95 (d, 1H), 4.81 (d, 1H), 3.63 (dd, 1H), 3.25 (dd, 1H), 3.05-2.90 (m, 3H), 2.70-2.63 (m, 2H). MS (EI) for C28H26ClN5O3. found 515.9 (MH+).

Sources & evidence

ORD record
ord-4e65dbf826804ad0a559b81ea587f742
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…