Sodium methanethiolate → HCID 10476716, compound

HRID 2293921Notes

Reaction equation

HRID 2293921 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:11])=[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([I:20])[CH:15]=2)[N:3]=1.[CH3:21][S-:22].[Na+]>CN(C=O)C>[I:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][NH:12][C:4]1[N:3]=[C:2]([S:22][CH3:21])[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[CH3:11]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 10340909HCID 10340909, compound

Product 1

HCID 10476716HCID 10476716, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of compound 6 (24.4 mg, 0.061 mmol) and sodium thiomethoxide (8 mg, 0.1 mmol) in DMF (1.5 mL) was heated for 22 h at 110° C. After cooling, the reaction mixture was concentrated to dryness and the residue was purified by a silica gel column chromatography (chloroform-methanol, 20:1) to give compound 16 (13 mg, 52.0%) as a colorless solid. 1H NMR (DMSO-d6) δ 3.06 (s, 6 H, N(CH3)2), 3.56 (s, 3 H, CH3), 4.58 (br s, 2 H, CH2), 7.10 (pseudo t, J=7.9 and 7.6 Hz, 1 H, H-16), 7.38 (d, J=7.6 Hz, 1 H, H-17), 7.56 (d, J=7.9 Hz, 1 H, H-15), 7.76 (s, 1 H, H-13), 7.69 (s, 1 H, H-8), 7.90 (br s, 1 H, exchangeable with D2O, NH).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated to dryness
  3. customthe residue was purified by a silica gel column chromatography (chloroform-methanol, 20:1)

Sources & evidence

ORD record
ord-f4e61784d696400694bae1039b7c46fc
Source dataset
uspto-grants-1997_11
Patent number
US05688774

Reaction notes

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