Sodium Methoxide → HCID 69586487, compound

HRID 723241Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([S:14]([C:17]3[CH:18]=[C:19]([C:24]#[N:25])[S:20][C:21]=3[S:22][CH3:23])(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=2)[CH2:4][CH2:3]1.[CH3:26][O-:27].[Na+]>O.CO>[CH3:26][O:27][C:24]([C:19]1[S:20][C:21]([S:22][CH3:23])=[C:17]([S:14]([C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)[CH:9]=2)(=[O:16])=[O:15])[CH:18]=1)=[NH:25]

Participants

Conditions

Temperature: 50 °C

Procedure

To a flask containing 15 mg (0.03 mmol) of 4-[3-(4-methyl-piperazin-1-yl)-benzenesulfonyl]-5-methylsulfanyl-thiophene-2-carbonitrile (Example 292: step a) was added 1 mL of MeOH and the resultant solution was treated with 1 mL 2M NaOMe in MeOH (2 mmol) at room temperature. The reaction was heated to 50° C. for 2 h. At this time it was cooled to room temperature and 2 drops of H2O was added. Concentration of the mixture in vacuo 5 followed by purification by preparative TLC (5% MeOH-CHCl3) yielded 12 mg (74%) of 4-[3-(4-methyl-piperazin-1-yl)-benzenesulfonyl]-5-methylsulfanyl-thiophene-2-carboximidic acid methyl ester as a yellow solid.

Workup

temperatureAt this time it was cooled to room temperature
customConcentration of the mixture in vacuo 5 followed by purification by preparative TLC (5% MeOH-CHCl3)

Sources & evidence

ORD record: ord-1a57bc9ea0fd43c79666773541560574
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138530B2

Reaction notes

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