Sodium methanethiolate → HCID 70978427, compound

HRID 2281060Notes

Reaction equation

HRID 2281060 reaction equation
Br[C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]1[CH:29]=[CH:28][C:18]([CH2:19][N:20]2[CH2:24][C:23](=[O:25])[N:22]([CH3:26])[C:21]2=[O:27])=[C:17]([F:30])[CH:16]=1.[CH3:31][S-:32].[Na+]>CN(C=O)C.ClCCl>[CH:12]1([CH2:11][N:7]2[C:6]3[CH:5]=[CH:4][C:3]([C:15]4[CH:29]=[CH:28][C:18]([CH2:19][N:20]5[CH2:24][C:23](=[O:25])[N:22]([CH3:26])[C:21]5=[O:27])=[C:17]([F:30])[CH:16]=4)=[C:2]([S:32][CH3:31])[C:10]=3[N:9]=[N:8]2)[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 70978654HCID 70978654, compound

Product 1

HCID 70978427HCID 70978427, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1-{4-[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]-2-fluorobenzyl}-3-methylimidazolidine-2,4-dione (10 mg, 0.021 mmol) in DMF (0.18 mL) was added sodium thiomethoxide (5.6 mg, 0.080 mmol, 4 equiv.). The mixture was stirred at 120° C. for 3.5 hours, cooled to ambient temperature and diluted with dichloromethane, which was washed with water and brine. The organic extract was dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified via silica gel chromatography (ethyl acetate/hexane gradient), providing the titled compound: 1H NMR (400 MHz, CDCl3) 7.39-7.45 (m, 2H), 7.34 (d, 1H, J=8.4 Hz), 7.18-7.24 (m, 2H), 4.70 (s, 2H), 4.53 (d, 2H, J=7.1 Hz), 3.90 (s, 2H), 3.06 (s, 3H), 2.85 (s, 3H), 1.40-1.46 (m, 1H), 0.67-0.71 (m, 2H), 0.50-0.54 (m, 2H) ppm. LRMS m/z (M+H) 440.2 found, 440.1 required.

Workup

  1. temperaturecooled to ambient temperature
  2. washwas washed with water and brine
  3. extractionThe organic extract
  4. dry with materialwas dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via silica gel chromatography (ethyl acetate/hexane gradient)

Sources & evidence

ORD record
ord-e48b59e95aa34abc885e8d053f4071ea
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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