1-Hydroxybenzotriazole → HCID 22012581, compound

HRID 1533820Notes

Reaction equation

HRID 1533820 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([C:12](=[O:37])[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])[CH:9]=[CH:8][C:4]=1[C:5](O)=[O:6].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[NH2:60][C:61]1[C:69]2[N:68]=[C:67]([CH2:70][N:71]3[CH2:76][CH2:75][N:74]([CH3:77])[CH2:73][CH2:72]3)[NH:66][C:65]=2[CH:64]=[CH:63][CH:62]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([CH:9]=[CH:8][C:4]=1[C:5](=[O:6])[NH:60][C:61]1[C:69]2[N:68]=[C:67]([CH2:70][N:71]3[CH2:72][CH2:73][N:74]([CH3:77])[CH2:75][CH2:76]3)[NH:66][C:65]=2[CH:64]=[CH:63][CH:62]=1)[C:12]([N:13]([CH3:36])[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=1[O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([N:29]1[CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH2:34]1)=[O:28])=[O:37]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18354839HCID 18354839, compoundHCID 18355157HCID 18355157, compound

Product 1

HCID 22012581HCID 22012581, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methoxy-4-[N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]-carbamoyl]benzoic acid (200 mg) in N,N-dimethylformamide (3 ml) at 0° C. were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (97 mg), N-hydroxybenzotriazole (79 mg) and 4-amino-2-[(4-methylpiperazin-1-yl)methyl]-1H-benzimidazole (105 mg) and the mixture was stirred at ambient temperature for 15 hours. The reaction mixture was poured into saturated sodium bicarbonate aqueous solution and extracted with chloroform. The organic layer was washed with saturated sodium bicarbonate aqueous solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1) to give 3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]-4-[2-[(4-methylpiperazin-1-yl)methyl]-1H-benzimidazol-4-yl]carbamoylbenzamide (104 mg).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated sodium bicarbonate aqueous solution and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-573095434fa34710bc79b4d223409270
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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