2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride → HCID 67009793, compound

HRID 1630190Notes

Reaction equation

HRID 1630190 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:40]=[CH:39][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]([CH2:31][C:32]4[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=4)[CH2:28][NH:27]3)=[O:25])=[CH:19][CH:18]=2)=[C:14]([CH3:41])[CH:13]=1>>[N:2]1([CH2:7][C:8]([N:27]2[CH2:28][C@H:29]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=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:39]=[CH:40][C:12]([F:11])=[CH:13][C:14]=3[CH3:41])=[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 67009367(2S,4R)-N-(4-(4-fluoro-2-methylphenoxy)phenyl)-4-(4-fluorobenzyl)pyrrolidine-2-carboxamide

Product 1

HCID 67009793HCID 67009793, compoundYield 42%

Procedure

Proceeding as in Example 1, but substituting 2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride and (2S,4R)—N-(4-(4-fluoro-2-methylphenoxy)phenyl)-4-(4-fluorobenzyl)pyrrolidine-2-carboxamide, gave Compound 74, (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-N-(4-(4-fluoro-2-methylphenoxy)phenyl)-4-(4-fluorobenzyl)pyrrolidine-2-carboxamide (189 mg, 42%). 1H-NMR (400 MHz, CDCl3): σ 8.96 (s, 1H), 8.23 (s, 1H), 7.99 (s, 1H), 7.37 (d, 2H), 7.17-7.14 (m, 2H), 7.01 (t, 2H), 6.96-6.93 (m, 1H), 6.83-6.76 (m, 4H), 5.02 (d, 1H), 4.95 (d, 1H), 4.80 (d, 1H), 3.63 (t, 1H), 3.23 (t, 1H), 3.03-2.86 (m, 2H), 2.69-2.60 (m, 2H), 2.18 (s, 3H), 1.72-1.57 (m, 1H). MS (EI) for C29H27F2N5O3. found 532.2 (MH+).

Sources & evidence

ORD record
ord-0776d07b776b455d8f8000952877d0bf
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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