Dichloromethane → HCID 58941825, compound

HRID 1845769Notes

Reaction equation

HRID 1845769 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[N:13]=[N:14][S:15][C:16]=2[CH2:17][O:18][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])=[S:11])[CH:5]=[CH:6][C:7]=1[F:8].[CH2:29](Cl)Cl.CCN(C(C)C)C(C)C.FC(F)(F)S(OC)(=O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]([C:12]2[N:13]=[N:14][S:15][C:16]=2[CH2:17][O:18][Si:19]([CH:23]([CH3:25])[CH3:24])([CH:26]([CH3:28])[CH3:27])[CH:20]([CH3:21])[CH3:22])[S:11][CH3:29])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 9526Methyl triflateHCID 81531DiisopropylethylamineHCID 58941925HCID 58941925, compound

Product 1

HCID 58941825HCID 58941825, compound

Procedure

To a solution of N-(3-chloro-4-fluorophenyl)-5-[(triisopropylsilyl)oxy]methyl-1,2,3-thia-diazole-4-carbothioamide (0.18 g, 0.00039 mol) in anhydrous DCM (3 mL, 0.04 mol) under N2 was added DIPEA (82 μL, 0.00047 mol) followed by methyl trifluoromethanesulfonate (47 μL, 0.00043 mol). The reaction was stirred for 5 minutes and then concentrated in vacuo. The crude material was used in the next step. The product amount was estimated (185 mg, 100%). MF=C20H29ClFN3OS2Si; LCMS calculated for C20H30ClFN3OS2Si (M+H)+: m/z=474.1.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4cd4c03f6779415494a10e93c790f196
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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