2-(1H-1,2,4-triazol-1-yl)acetic acid hydrochloride → HCID 67009888, compound

HRID 1630191Notes

Reaction equation

HRID 1630191 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)=[CH:14][C:13]=1[CH3:41]>>[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])=[C:13]([CH3:41])[CH:14]=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 67009472(2S,4R)-N-(4-(4-fluoro-3-methylphenoxy)phenyl)-4-(4-fluorobenzyl)pyrrolidine-2-carboxamide

Product 1

HCID 67009888HCID 67009888, compoundYield 84%

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-3-methylphenoxy)phenyl)-4-(4-fluorobenzyl)pyrrolidine-2-carboxamide, gave Compound 73, (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-N-(4-(4-fluoro-3-methylphenoxy)phenyl)-4-(4-fluorobenzyl)pyrrolidine-2-carboxamide (149 mg, 84%). 1H-NMR (400 MHz, CDCl3): σ 8.90 (s, 1H), 8.24 (s, 1H), 7.99 (s, 1H), 7.40 (d, 2H), 7.17-7.14 (m, 2H), 7.00 (t, 2H), 6.95-6.88 (m, 3H), 6.79-6.72 (m, 2H), 5.03 (d, 1H), 4.95 (d, 1H), 4.80 (d, 1H), 3.64 (t, 1H), 3.23 (t, 1H), 3.05-2.85 (2H), 2.69-2.61 (m, 2H), 2.22 (s, 3H), 1.72-1.67 (m, 1H). MS (EI) for C29H27F2N5O3. found 530.2 (MH−).

Sources & evidence

ORD record
ord-af851469e7294834952110c6258cf9df
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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