(1H-1,2,3-Triazol-1-yl)acetic acid--hydrogen chloride (1/1) → HCID 67009269, compound

HRID 1630254Notes

Reaction equation

HRID 1630254 reaction equation
Cl.[N:2]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][N:4]=[N:3]1.[Cl:11][C:12]1[S:16][C:15]([CH2:17][C@H:18]2[CH2:22][NH:21][C@H:20]([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])[CH2:19]2)=[CH:14][CH:13]=1>>[N:2]1([CH2:7][C:8]([N:21]2[CH2:22][C@H:18]([CH2:17][C:15]3[S:16][C:12]([Cl:11])=[CH:13][CH:14]=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:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=3)=[CH:28][CH:27]=2)=[O:24])=[O:10])[CH:6]=[CH:5][N:4]=[N:3]1

Participants

3

Reactant 2

HCID 45357676(1H-1,2,3-Triazol-1-yl)acetic acid--hydrogen chloride (1/1)HCID 46901320HCID 46901320, compound

Product 1

HCID 67009269HCID 67009269, compoundYield 65%

Procedure

Proceeding as in Example 1, but substituting 2-(1H-1,2,3-triazol-1-yl)acetic acid hydrochloride and (2S,4S)-4-((5-chlorothien-2-yl)methyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 65, (2S,4S)-1-(2-(1H-1,2,3-triazol-1-yl)acetyl)-4-((5-chlorothien-2-yl)methyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (60.2 mg, 65%). 1H-NMR (400 MHz, CDCl3): σ 8.95 (s, 1H), 7.77 (d, 2H), 7.43 (d, 2H), 7.00 (t, 2H), 6.94-6.89 (m, 4H), 6.76 (d, 1H), 6.63 (d, 1H), 5.30 (d, 1H), 5.17 (d, 1H), 4.80 (d, 1H), 3.79 (dd, 1H), 3.30 (t, 1H), 3.04-2.93 (m, 2H), 2.87-2.78 (m, 1H), 2.68 (dd, 1H), 1.75-1.68 (m, 1H). MS (EI) for C26H23ClFN5O3S. found 540.1 (MH+).

Sources & evidence

ORD record
ord-a693ea23904d436fa826164b39dc5ba6
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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