2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride → HCID 46190696, compound

HRID 1630177Notes

Reaction equation

HRID 1630177 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:40]=[CH:39][C:15]([CH2:16][C@H:17]2[CH2:21][NH:20][C@H:19]([C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]4[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=4)=[CH:27][CH:26]=3)=[O:23])[CH2:18]2)=[CH:14][CH:13]=1>>[N:2]1([CH2:7][C:8]([N:20]2[CH2:21][C@H:17]([CH2:16][C:15]3[CH:39]=[CH:40][C:12]([F:11])=[CH:13][CH:14]=3)[CH2:18][C@H:19]2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=3)=[CH:27][CH:26]=2)=[O:23])=[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 670100921222196-66-8

Product 1

HCID 46190696HCID 46190696, compoundYield 33%

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)pyrrolidine-2-carboxamide, gave Compound 141, (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-(4-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (39 mg, 33%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.00 (s, 1H), 8.43 (s, 1H), 7.95 (s, 1H), 7.57 (d, 2H), 7.35-7.08 (m, 7H), 7.05-6.90 (m, 4H), 5.23 (q, 2H), 4.56-4.47 (m, 1H), 3.87-3.74 (m, 1H), 3.39-3.29 (m, 1H), 2.79-2.62 (m, 3H), 2.04-1.89 (m, 2H). MS (EI) for C28H25F2N5O3. found 517.9 (MH+).

Sources & evidence

ORD record
ord-fd61a34b51af444bbdc72e932c4dfd6d
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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