Tetrahydrofuran → HCID 11598087, compound

HRID 555402Notes

Reaction equation

HRID 555402 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:10]=[CH:9][C:7](C)([NH2:8])[CH2:6][CH:5]=1.[C:14]([C:18]1[CH:33]=[CH:32][CH:31]=[CH:30][C:19]=1[O:20][C:21]1[C:26]([N:27]=[C:28]=[S:29])=[CH:25][CH:24]=[CH:23][N:22]=1)([CH3:17])([CH3:16])[CH3:15].[CH2:34]1COCC1>>[C:14]([C:18]1[CH:33]=[CH:32][CH:31]=[CH:30][C:19]=1[O:20][C:21]1[C:26]([NH:27][C:28]([NH:8][C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:12])[F:13])=[CH:10][C:9]=2[CH3:34])=[S:29])=[CH:25][CH:24]=[CH:23][N:22]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 59857388HCID 59857388, compoundHCID 66987541HCID 66987541, compound

Product 1

HCID 11598087HCID 11598087, compoundYield 45%

Conditions

Temperature
60 °C

Procedure

To a solution of 4-trifluoromethoxy-1-methyl-aniline (32 mg, 0.17 mmol) in THF (1 mL) was slowly added 1c (40 mg, 0.14 mmol). The reaction was stirred 18 h at 60° C. and concentrated. The residue was purified by column chromatography on silica gel using a continuous gradient from 0% to 40% ethyl acetate in hexanes as eluent to afford 105a (36 mg, 45%). [M+H]+=476.08.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography on silica gel using a continuous gradient from 0% to 40% ethyl acetate in hexanes as eluent

Sources & evidence

ORD record
ord-f5d42f475edb43d59e6272fb95d68a42
Source dataset
uspto-grants-2011_11
Patent number
US08053450B2

Reaction notes

Loading…