(1H-1,2,3-Triazol-1-yl)acetic acid--hydrogen chloride (1/1) → HCID 45256217, compound

HRID 1630187Notes

Reaction equation

HRID 1630187 reaction equation
Cl.[N:2]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][N:4]=[N:3]1.F[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)=[CH:14][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][CH:12]=[CH:13][CH:14]=3)[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:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=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 67010092(2S,4R)-4-(4-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

Product 1

HCID 45256217HCID 45256217, compoundYield 44%

Procedure

Proceeding as in Example 1, but substituting 2-(1H-1,2,3-triazol-1-yl)acetic acid hydrochloride and (2S,4R)-4-(4-fluorobenzyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 10, (2S,4R)-1-(2-(1H-1,2,3-triazol-1-yl)acetyl)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (75.2 mg, 44%). Major isomer: 1H-NMR (400 MHz, CDCl3): δ 9.00 (s, 1H), 7.74 (d, 2H), 7.42-7.17 (m, 7H), 7.03-6.83 (m, 6H), 5.28 (d, 1H), 5.12 (d, 1H), 4.73 (d, 1H), 3.71-64 (m, 1H), 3.31-3.22 (m, 1H), 3.006-2.93 (m, 1H), 2.89 (dd, 1H), 2.71-2.64 (m, 1H), 2.52 (dd, 1H), 1.79-1.70 (m, 1H). MS (EI) for C28H27FN5O3 found 500 (MH+).

Sources & evidence

ORD record
ord-c47370fc341448e081ef5348834f8103
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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