2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride → HCID 45376098, compound

HRID 1630179Notes

Reaction equation

HRID 1630179 reaction equation
Cl.[N:2]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[N:5][CH:4]=[N:3]1.[Cl:11][C:12]1[CH:40]=[C:39]([Cl:41])[CH:38]=[CH:37][C:13]=1[CH2:14][C@H:15]1[CH2:19][NH:18][C@H:17]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)=[CH:25][CH:24]=2)=[O:21])[CH2:16]1>>[N:2]1([CH2:7][C:8]([N:18]2[CH2:19][C@H:15]([CH2:14][C:13]3[CH:37]=[CH:38][C:39]([Cl:41])=[CH:40][C:12]=3[Cl:11])[CH2:16][C@H:17]2[C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)=[CH:25][CH:24]=2)=[O:21])=[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 67010008HCID 67010008, compound

Product 1

HCID 45376098HCID 45376098, compoundYield 35%

Procedure

Proceeding as in Example 1, but substituting 2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride and (2S,4R)-4-(2,4-dichlorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 180, (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-(2,4-dichlorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (48 mg, 35%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.03 (s, 1H), 8.43 (s, 1H), 7.96 (s, 1H), 7.68-7.35 (m, 5H), 7.19 (t, 2H), 7.07-6.88 (m, 4H), 5.24 (q, 2H), 4.57-4.48 (m, 1H), 3.91-3.78 (m, 1H), 2.97-2.70 (m, 3H), 2.11-1.88 (m, 3H). MS (EI) for C28H24FN5O3. found 569.8 (MH+).

Sources & evidence

ORD record
ord-1dd8061150044be08cad5fdeb60d2ce4
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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