2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride → HCID 67010802, compound

HRID 1630239Notes

Reaction equation

HRID 1630239 reaction equation
Cl.[N:2]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[N:5][CH:4]=[N:3]1.[F:11][C:12]1[CH:41]=[CH:40][C:15]([CH2:16][C@H:17]2[C:21](=[O:22])[NH:20][C@H:19]([C:23]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][C:33]4[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=4)=[CH:28][CH:27]=3)=[O:24])[CH2:18]2)=[CH:14][CH:13]=1>>[N:2]1([CH2:7][C:8]([N:20]2[C:21](=[O:22])[C@H:17]([CH2:16][C:15]3[CH:40]=[CH:41][C:12]([F:11])=[CH:13][CH:14]=3)[CH2:18][C@H:19]2[C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=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 67009808HCID 67009808, compound

Product 1

HCID 67010802HCID 67010802, compoundYield 4%

Procedure

Proceeding as in Example 1, but substituting 2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride and (2S,4R)-4-(4-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)-5-oxopyrrolidine-2-carboxamide, gave Compound 71, (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-(4-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)-5-oxopyrrolidine-2-carboxamide (18.2 mg, 4%). 1H-NMR (400 MHz, CDCl3): σ 8.17 (s, 1H), 8.01 (s, 1H), 7.79 (s, 1H), 7.39 (d, 2H), 7.19-7.15 (m, 1H), 7.04-6.99 (m, 4H), 9.95-6.91 (m, 4H), 5.67 (d, 1H), 5.59 (d, 1H), 4.67 (d, 1H), 3.48-3.40 (m, 1H), 3.25 (dd, 1H), 2.78 (dd, 1H), 2.46 (dd, 1H), 2.06-1.97 (m, 1H). MS (EI) for C28H23F2N5O4. found 532.2 (MH+).

Sources & evidence

ORD record
ord-007cc02ee273447884f19417dc299bf1
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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