(Bis(2-methoxyethyl)amino)sulfur trifluoride → HCID 90415452, compound

HRID 578846Notes

Reaction equation

HRID 578846 reaction equation
[F:1][CH:2]([F:26])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]([CH2:18][N:19]3[CH:23]=[N:22][C:21]([CH2:24]O)=[N:20]3)[CH:13]=[N:14][C:15]=2[O:16][CH3:17])[CH:7]=[CH:8][CH:9]=1.COCCN(S(F)(F)[F:37])CCOC>C(Cl)Cl>[F:1][CH:2]([F:26])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[C:15]([O:16][CH3:17])=[N:14][CH:13]=[C:12]([CH2:18][N:19]3[CH:23]=[N:22][C:21]([CH2:24][F:37])=[N:20]3)[CH:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 90415570HCID 90415570, compound

Product 1

HCID 90415452HCID 90415452, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-((5-(3-(difluoromethoxy)phenyl)-6-methoxypyridin-3-yl)methyl)-1H-1,2,4-triazol-3-yl)methanol (Example 202, 40.0 mg, 0.11 mmol) in DCM (3 mL) was added Deoxo-Fluor® (36.64 mg, 0.17 mmol). The mixture was stirred at room temperature for 2 h. The material was adsorbed on silica and purified (FCC, SiO2, 20-100% EtOAc/hexanes) to afford the title compound (11 mg, 27%). 1H NMR (400 MHz, CD3OD) δ 8.61 (s, 1H), 8.21 (d, J=2.3 Hz, 1H), 7.77 (d, J=2.3 Hz, 1H), 7.49-7.36 (m, 2H), 7.33 (t, J=2.2 Hz, 1H), 7.16-7.11 (m, 1H), 7.04-6.65 (m, 1H), 5.44 (s, 2H), 5.41-5.28 (m, 2H), 3.96 (s, 3H). [M+H]=365.21.

Workup

  1. custompurified (FCC, SiO2, 20-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-628522efa0184043b982a85483321f17
Source dataset
uspto-grants-2015_05
Patent number
US09040692B2

Reaction notes

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