1,1'-Thiocarbonyldiimidazole → HCID 178492695, compound

HRID 1533757Notes

Reaction equation

HRID 1533757 reaction equation
[NH2:1][C:2]1[C:44]([NH2:45])=[CH:43][CH:42]=[CH:41][C:3]=1[C:4]([NH:6][C:7]1[CH:38]=[CH:37][C:10]([C:11]([N:13]([CH3:36])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([N:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)=[O:28])=[O:12])=[CH:9][C:8]=1[O:39][CH3:40])=[O:5].[C:46](N1C=CN=C1)(N1C=CN=C1)=[S:47]>O1CCCC1>[SH:47][C:46]1[NH:45][C:44]2[CH:43]=[CH:42][CH:41]=[C:3]([C:4]([NH:6][C:7]3[CH:38]=[CH:37][C:10]([C:11]([N:13]([CH3:36])[C:14]4[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=4[O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([N:29]4[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]4)=[O:28])=[O:12])=[CH:9][C:8]=3[O:39][CH3:40])=[O:5])[C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 183547944-(2,3-diaminophenyl)carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide

Product 1

HCID 178492695HCID 178492695, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2,3-diaminobenzoyl)amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (110 mg) in anhydrous tetrahydrofuran (2 ml) was added 1,1′-thiocarbonyldiimidazole (48 mg) under nitrogen at ambient temperature and stirred at same temperature for 1 day. After being concentrated in vacuo, the residue was diluted with a mixture of chloroform and saturated sodium bicarbonate aqueous solution and the organic layer was separated. The organic layer was washed with water and brine and the solution was dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by preparative thin-layer chromatography (ethyl acetate-methanol=1:1) to give 4-(2-mercapto-1H-benzimidazol-4-yl)carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (96 mg) as a powder.

Workup

  1. concentrationAfter being concentrated in vacuo
  2. additionthe residue was diluted with a mixture of chloroform and saturated sodium bicarbonate aqueous solution
  3. customthe organic layer was separated
  4. washThe organic layer was washed with water and brine
  5. dry with materialthe solution was dried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was purified by preparative thin-layer chromatography (ethyl acetate-methanol=1:1)

Sources & evidence

ORD record
ord-a42d87b513954bcdb36b2a57b99e7c39
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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