(1H-1,2,3-Triazol-1-yl)acetic acid--hydrogen chloride (1/1) → HCID 67009099, compound

HRID 1630248Notes

Reaction equation

HRID 1630248 reaction equation
Cl.[N:2]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][N:4]=[N:3]1.[F:11][C:12]1[CH:40]=[CH:39][C:15]([CH2:16][C@H:17]2[CH2:21][NH:20][C@H:19]([C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]4[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=4)=[CH:27][CH:26]=3)=[O:23])[CH2:18]2)=[C:14]([CH3:41])[CH:13]=1>>[N:2]1([CH2:7][C:8]([N:20]2[CH2:21][C@H:17]([CH2:16][C:15]3[CH:39]=[CH:40][C:12]([F:11])=[CH:13][C:14]=3[CH3:41])[CH2:18][C@H:19]2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=3)=[CH:27][CH:26]=2)=[O:23])=[O:10])[CH:6]=[CH:5][N:4]=[N:3]1

Participants

3

Reactant 2

HCID 45357676(1H-1,2,3-Triazol-1-yl)acetic acid--hydrogen chloride (1/1)HCID 67009160(2S,4R)-4-(4-fluoro-2-methylbenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

Product 1

HCID 67009099HCID 67009099, compoundYield 46%

Procedure

Proceeding as in Example 1, but substituting 2-(1H-1,2,3-triazol-1-yl)acetic acid hydrochloride and (2S,4R)-4-(4-fluoro-2-methylbenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 6, (2S,4R)-1-(2-(1H-1,2,3-triazol-1-yl)acetyl)-4-(4-fluoro-2-methylbenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (142 mg, 46%). Major isomer: 1H-NMR (400 MHz, CDCl3): δ 8.96 (s, 1H), 7.76 (d, 2H), 7.40 (d, 2H), 7.11-6.83 (m, 9H), 5.31 (d, 1H), 5.15 (d, 1H), 4.77 (d, 1H), 3.71 (t, 1H), 3.30 (t, 1H), 3.02-2.91 (m, 1H), 2.82 (dd, 1H), 2.71 (dd, 1H), 2.57 (dd, 1H), 2.33 (s, 3H), 1.78-1.68 (m, 1H). MS (EI) for C29H28F2N5O3 found 532 (MH+).

Sources & evidence

ORD record
ord-eeaf601a331f459095391af81d7953fb
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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