2-(2H-1,2,3-triazol-2-yl)acetic acid hydrochloride → (2S,4R)-1-(2-(2H-1,2,3-triazol-2-yl)acetyl)-4-(3-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

HRID 1630245

Reaction equation

HRID 1630245 reaction equation
Cl.[N:2]1[N:3]([CH2:7][C:8]([OH:10])=O)[N:4]=[CH:5][CH:6]=1.[F:11][C:12]1[CH:13]=[C:14]([CH:38]=[CH:39][CH:40]=1)[CH2:15][C@H:16]1[CH2:20][NH:19][C@H:18]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)=[CH:26][CH:25]=2)=[O:22])[CH2:17]1>>[N:4]1[N:3]([CH2:7][C:8]([N:19]2[CH2:20][C@H:16]([CH2:15][C:14]3[CH:38]=[CH:39][CH:40]=[C:12]([F:11])[CH:13]=3)[CH2:17][C@H:18]2[C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=3)=[CH:26][CH:25]=2)=[O:22])=[O:10])[N:2]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 670094972-(2H-1,2,3-triazol-2-yl)acetic acid hydrochlorideHCID 67009746(2S,4R)-4-(3-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

Product 1

HCID 46191400(2S,4R)-1-(2-(2H-1,2,3-triazol-2-yl)acetyl)-4-(3-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideYield 39%

Procedure

Proceeding as in Example 1, but substituting 2-(2H-1,2,3-triazol-2-yl)acetic acid hydrochloride and (2S,4R)-4-(3-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 49, (2S,4R)-1-(2-(2H-1,2,3-triazol-2-yl)acetyl)-4-(3-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (74 mg, 39%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.96 (s, 1H), 7.79 (s, 2H), 7.57-7.51 (m, 2H), 7.38-7.29 (m, 1H), 7.22-6.90 (m, 10H), 5.56-5.41 (m, 2H), 4.52-4.54 (m, 1H), 3.84-3.77 (m, 1H), 2.79-2.63 (m, 3H), 2.01-1.87 (m, 2H). MS (EI) for C28H25F2N5O3. found 517.9 (MH+).

Sources & evidence

ORD record
ord-0711e5ee51ad4c7dba315c8297295288
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Linked notes

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