HCID 46735946, compound → (2S,4R)-1-(2-(5-amino-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)acetyl)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

HRID 1630185Notes

Reaction equation

HRID 1630185 reaction equation
Cl.[NH2:2][C:3]1[N:7]([CH2:8][C:9]([OH:11])=O)[N:6]=[C:5]([C:12]([F:15])([F:14])[F:13])[N:4]=1.[CH2:16]([C@H:23]1[CH2:27][NH:26][C@H:25]([C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)=[CH:33][CH:32]=2)=[O:29])[CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[NH2:2][C:3]1[N:7]([CH2:8][C:9]([N:26]2[CH2:27][C@H:23]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:24][C@H:25]2[C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)=[CH:33][CH:32]=2)=[O:29])=[O:11])[N:6]=[C:5]([C:12]([F:15])([F:14])[F:13])[N:4]=1

Participants

3

Reactant 2

HCID 46735946HCID 46735946, compoundHCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

Product 1

HCID 67009377(2S,4R)-1-(2-(5-amino-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)acetyl)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideYield 51%

Procedure

Proceeding as in Example 1, but substituting 2-(5-amino-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 11, (2S,4R)-1-(2-(5-amino-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)acetyl)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (100.1 mg, 51%). Major isomer: 1H-NMR (400 MHz, CDCl3): δ 8.90 (s, 1H), 7.37-7.14 (m, 7H), 7.02-6.81 (m, 6H), 5.43 (s, 2H), 4.82 (d, 1H), 4.73 (d, 1H), 4.65 (d, 1H), 3.71 (t, 1H), 3.24 (t, 1H), 3.02-2.90 (m, 1H), 2.80 (dd, 1H), 2.65 (dd, 1H), 2.38 (dd, 1H), 1.99 (br s, 2H), 1.81-1.71 (m, 1H). MS (EI) for C29H27F4N6O3 found 583 (MH+).

Sources & evidence

ORD record
ord-cf0dad7d31234521a2704434262de8c3
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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