2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride → HCID 45377579, compound

HRID 1630237Notes

Reaction equation

HRID 1630237 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:38]=[CH:37][C:15]([O:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]([C@@H:26]3[CH2:30][C@@H:29]([CH2:31][C:32]4[CH:36]=[CH:35][S:34][CH:33]=4)[CH2:28][NH:27]3)=[O:25])=[CH:19][CH:18]=2)=[CH:14][CH:13]=1>>[N:2]1([CH2:7][C:8]([N:27]2[CH2:28][C@H:29]([CH2:31][C:32]3[CH:36]=[CH:35][S:34][CH:33]=3)[CH2:30][C@H:26]2[C:24]([NH:23][C:20]2[CH:21]=[CH:22][C:17]([O:16][C:15]3[CH:14]=[CH:13][C:12]([F:11])=[CH:38][CH:37]=3)=[CH:18][CH:19]=2)=[O:25])=[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 67009440(2S,4R)-N-(4-(4-fluorophenoxy)phenyl)-4-(thien-3-ylmethyl)pyrrolidine-2-carboxamide

Product 1

HCID 45377579HCID 45377579, compoundYield 35%

Procedure

Proceeding as in Example 1, but substituting 2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride and (2S,4R)—N-(4-(4-fluorophenoxy)phenyl)-4-(thien-3-ylmethyl)pyrrolidine-2-carboxamide, gave Compound 72, (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)-4-(thiophen-3-ylmethyl)pyrrolidine-2-carboxamide (172 mg, 35%). 1H-NMR (400 MHz, CDCl3): δ 9.03 (s, 1H), 8.24 (s, 1H), 7.99 (s, 1H), 7.42 (d, 2H), 7.32-7.30 (m, 1H), 7.03-6.90 (m, 8H), 5.05 (d, 1H), 4.97 (d, 1H), 4.81 (d, 1H), 3.87 (t, 1H), 3.24 (t, 1H), 3.05-2.97 (m, 1H), 2.96-2.89 (m, 1H), 2.77-2.64 (m, 2H), 1.73-1.65 (m, 1H). MS (EI) for C26H24FN5O3S found 505.9 (MH+).

Sources & evidence

ORD record
ord-e81005dcc3df42e58acd285629153594
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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