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

HRID 1630182Notes

Reaction equation

HRID 1630182 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]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=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]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=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 67009476(2S,4S)-N-(4-(4-fluorophenoxy)phenyl)-4-phenylpyrrolidine-2-carboxamide

Product 1

HCID 56954244(2S,4S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)-4-phenylpyrrolidine-2-carboxamideYield 68%

Procedure

Proceeding as in Example 1, but substituting 2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride and (2S,4S)—N-(4-(4-fluorophenoxy)phenyl)-4-phenylpyrrolidine-2-carboxamide, gave Compound 78, (2S,4S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)-4-phenylpyrrolidine-2-carboxamide (187 mg, 68%). 1H-NMR (400 MHz, CDCl3): σ 9.08 (s, 1H), 8.27 (s, 1H), 8.01 (s, 1H), 7.46 (d, 2H), 7.40-7.37 (m, 2H), 7.33-7.29 (m, 2H), 7.04-6.99 (m, 2H), 6.96-6.92 (m, 4H), 5.04 (d, 2H), 4.96 (d, 1H), 4.06 (t, 1H), 3.96-3.86 (m, 1H), 3.61 (t, 1H), 2.90 (dd, 1H), 2.20-2.11 (m, 1H). MS (EI) for C27H24FN5O3. found 486.2 (MH+).

Sources & evidence

ORD record
ord-68ff1b1e1e2b4010938b10ecd8389b7d
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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