Sodium methanethiolate → HCID 10159133, compound

HRID 719206Notes

Reaction equation

HRID 719206 reaction equation
[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:21]2[C:12](=[N:13][C:14]3[C:19]([N:20]=2)=[C:18]2[CH:22]=[CH:23][CH:24]=[C:25]([O:26][CH3:27])[C:17]2=[CH:16][CH:15]=3)[CH:11]=[C:10](Cl)[CH:9]=1)=[O:7].[CH3:30][S-:31].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:21]2[C:12](=[N:13][C:14]3[C:19]([N:20]=2)=[C:18]2[CH:22]=[CH:23][CH:24]=[C:25]([O:26][CH3:27])[C:17]2=[CH:16][CH:15]=3)[CH:11]=[C:10]([S:31][CH3:30])[CH:9]=1)=[O:7]

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 10112144HCID 10112144, compound

Product 1

HCID 10159133HCID 10159133, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 9-chloro-4-methoxy-benzo[a]phenazine-11-carboxylic acid (2-dimethylamino-ethyl)-amide (85 mg) and sodium thiomethoxide (43 mg) in N,N-dimethylformamide (1 mL) was heated to 120° C. for 6 hours and 60° C. for 16 hours. The reaction mixture was then cooled, diluted with ethyl acetate, washed with water, dried (MgSO4) and the solvent removed in vacuo to yield a yellow solid which was purified using flash chromatography to yield the desired title compound (37 mg).

Workup

  1. temperatureThe reaction mixture was then cooled
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customto yield a yellow solid which
  6. customwas purified

Sources & evidence

ORD record
ord-d6abcb515d914e5e9be627a16fd5ce56
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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