Methyl triflate → Methyl N-(3-chloro-4-fluorophenyl)-4-[(triisopropylsilyl)oxy]methyl-1,2,5-oxadiazole-3-carbimidothioate

HRID 1845738Notes

Reaction equation

HRID 1845738 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:16]([CH2:17][O:18][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])=[N:15][O:14][N:13]=2)=[S:11])[CH:5]=[CH:6][C:7]=1[F:8].[CH:29](N(CC)C(C)C)(C)C.FC(F)(F)S(OC)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]([C:12]2[C:16]([CH2:17][O:18][Si:19]([CH:23]([CH3:25])[CH3:24])([CH:26]([CH3:28])[CH3:27])[CH:20]([CH3:21])[CH3:22])=[N:15][O:14][N:13]=2)[S:11][CH3:29])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 9526Methyl triflateHCID 81531DiisopropylethylamineHCID 58941860N-(3-Chloro-4-fluorophenyl)-4-[(triisopropylsilyl)oxy]methyl-1,2,5-oxadiazole-3-carbothioamide

Product 1

HCID 58941961Methyl N-(3-chloro-4-fluorophenyl)-4-[(triisopropylsilyl)oxy]methyl-1,2,5-oxadiazole-3-carbimidothioate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(3-chloro-4-fluorophenyl)-4-[(triisopropylsilyl)oxy]methyl-1,2,5-oxadiazole-3-carbothioamide (3.3 g, 7.4 mmol) in anhydrous DCM (148 mL) under N2 was added N,N-diisopropylethylamine (DIPEA) (1.4 mL). Methyl trifluoromethanesulfonate (900 μL, 8.2 mmol) was then added dropwise and stirred for 2 hrs. The reaction was stripped to dryness and purified on a 330 g silica ISCO cartridge, eluting with 25% EtOAc/hexane to yield the desired product as a yellow oil that solidified upon standing. (2.97 g, 87%). 1H NMR (400 MHz, DMSO-d6) δ: 11.32 (s, 1H), 8.01 (dd, J=7.1, 2.7 Hz, 1H), 7.45 (dd, J=9.5, 9.5 Hz, 1H), 7.67 (m, 1H), 4.4 (s=3H), 5.13 (s, 2H), 1.1 (m, 3H); 0.99 (m, 18H); MF=C20H29ClFN3O2SSi; LCMS calculated for C20H30ClFN3O2SSi(M+H)+: m/z=458.150.

Workup

  1. custompurified on a 330 g silica ISCO cartridge
  2. washeluting with 25% EtOAc/hexane

Sources & evidence

ORD record
ord-b1a6736e8cb14c60bf5f85443e5bcc42
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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