1H-Benzotriazol-1-ol--ammonia (1/1) → HCID 22012581, compound

HRID 429695Notes

Reaction equation

HRID 429695 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.C1C=C2N=NN(O)C2=CC=1.N.[NH2:61][C:62]1[C:70]2[N:69]=[C:68]([CH2:71][N:72]3[CH2:77][CH2:76][N:75]([CH3:78])[CH2:74][CH2:73]3)[NH:67][C:66]=2[CH:65]=[CH:64][CH:63]=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:61][C:62]1[C:70]2[N:69]=[C:68]([CH2:71][N:72]3[CH2:73][CH2:74][N:75]([CH3:78])[CH2:76][CH2:77]3)[NH:67][C:66]=2[CH:65]=[CH:64][CH:63]=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 1131751H-Benzotriazol-1-ol--ammonia (1/1)HCID 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 2methoxy-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-hydroxybenzotrizole (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-9bb4e749fec043e38eb219b777168e3c
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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