HCID 46901320, compound → HCID 46191402, compound

HRID 1630253Notes

Reaction equation

HRID 1630253 reaction equation
Cl.[N:2]1[N:3]([CH2:7][C:8]([OH:10])=O)[N:4]=[CH:5][CH:6]=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:4]1[N:3]([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])[N:2]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 46901320HCID 46901320, compoundHCID 670094972-(2H-1,2,3-triazol-2-yl)acetic acid hydrochloride

Product 1

HCID 46191402HCID 46191402, compoundYield 58%

Procedure

Proceeding as in Example 1, but substituting 2-(2H-1,2,3-triazol-2-yl)acetic acid hydrochloride and (2S,4S)-4-((5-chlorothien-2-yl)methyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 66, (2S,4S)-1-(2-(2H-1,2,3-triazol-2-yl)acetyl)-4-((5-chlorothien-2-yl)methyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (58.3 mg, 58%). 1H-NMR (400 MHz, CDCl3): σ 9.14 (s, 1H), 7.72 (s, 2H), 7.42 (d, 2H), 7.00 (t, 2H), 6.95-6.90 (m, 4H), 6.75 (d, 1H), 6.61 (d, 1H), 5.39 (s, 2H), 4.86 (d, 1H), 3.62 (dd, 1H), 3.19 (t, 1H), 3.03-2.85 (m, 2H), 2.83-2.77 (m, 1H), 2.72 (dd, 1H), 1.72-1.64 (m, 1H). MS (EI) for C26H23ClFN5O3S. found 540.1 (MH+).

Sources & evidence

ORD record
ord-8714edfc19f14f68911bacb3dca5a7dd
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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