Trifluoroacetic acid → 4-(phenylthio)-3-({3-[4-(pyridin-2-ylamino)butyl]-1,2,4-oxadiazol-5-yl}methyl)butanoic Acid Trifluoroacetate

HRID 585567Notes

Reaction equation

HRID 585567 reaction equation
[C:1]1([S:7][CH2:8][CH:9]([CH2:18][C:19]2[O:23][N:22]=[C:21]([CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)[N:20]=2)[CH2:10][C:11]([O:13]C(C)(C)C)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>ClCCl>[F:38][C:37]([F:40])([F:39])[C:35]([OH:41])=[O:36].[C:1]1([S:7][CH2:8][CH:9]([CH2:18][C:19]2[O:23][N:22]=[C:21]([CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)[N:20]=2)[CH2:10][C:11]([OH:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21927896Tert-butyl 4-(phenylthio)-3-({3-[4-(pyridin-2-ylamino)butyl]-1,2,4-oxadiazol-5-yl}methyl)butanoate

Product 1

HCID 695905034-(phenylthio)-3-({3-[4-(pyridin-2-ylamino)butyl]-1,2,4-oxadiazol-5-yl}methyl)butanoic Acid TrifluoroacetateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from step 3 (50.4 mg, 0.10 mmoles) was stirred at RT in 1:1 mix of TFA and dichloromethane (2 mL) for 30 min. The solvent was removed under reduced pressure to give the product 56.2 mg (99%). 1H NMR (CD3OD) δ 7.84-7.79 (m, 2H), 7.39-7.35 (m, 2H), 7.32-7.26 (m, 2H), 7.22-7.17 (t, 1H), 6.95 (d, 1H), 6.82 (t, 1H), 3.37 (t, 2H), 3.22-3.02 (series of m, 4H), 2.81 (t, 2H), 2.65-2.57 (series of m, 2H), 2.49 (t, 1H), 1.92-1.82 (series of m, 2H), 1.80-1.72 (series of m, 2H); MS (ESI+) for C22H26N4O3S m/z 427 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-29a6644021ce4d4d977a6e15f59de578
Source dataset
uspto-grants-2005_08
Patent number
US06933304B2

Reaction notes

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