1-Hydroxybenzotriazole → HCID 18355220, compound

HRID 1533811Notes

Reaction equation

HRID 1533811 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=1[N:17]([CH3:49])[C:18](=[O:48])[C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([C:28]2[C:36]3[N:35]=[C:34]([CH2:37][NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[NH:33][C:32]=3[CH:31]=[CH:30][CH:29]=2)=[O:27])=[C:21]([O:46][CH3:47])[CH:20]=1)(O)=[O:2].[C:50]([O:54][C:55]([N:57]1[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]1)=[O:56])([CH3:53])([CH3:52])[CH3:51].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[CH3:47][O:46][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[NH:25][C:26]([C:28]1[C:36]2[N:35]=[C:34]([CH2:37][NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[NH:33][C:32]=2[CH:31]=[CH:30][CH:29]=1)=[O:27])[C:18]([N:17]([CH3:49])[C:11]1[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:10]=1[O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:1]([N:60]1[CH2:61][CH2:62][N:57]([C:55]([O:54][C:50]([CH3:53])([CH3:51])[CH3:52])=[O:56])[CH2:58][CH2:59]1)=[O:2])=[O:48]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18354945HCID 18354945, compound

Product 1

HCID 18355220HCID 18355220, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-[2-(5-carboxypent-1-yloxy)-4-methylphenyl]-3-methoxy-N-methyl-4-[2-(tert-butoxycarbonylamino)methyl-1H-benzimidazol-4-yl]carbonylaminobenzamide (200 mg), 4-(tert-butoxycarbonyl)piperazine (66.3 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (68.3 mg) and 1-hydroxybenztriazol (48.1 mg) in N,N-dimethylformamide (5 ml) was stirred at ambient temperature overnight and the mixture was diluted with ethyl acetate. The solution was washed successively with saturated aqueous sodium hydrogen carbonate solution, water and brine and dried over magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column (chloroform) to give 3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-tert-butoxycarbonylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]-4-[2-(tert-butoxycarbonyl)aminomethyl-1H-benzimidazol-4-yl]carbonylaminobenzamide (250 mg).

Workup

  1. washThe solution was washed successively with saturated aqueous sodium hydrogen carbonate solution, water and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel column (chloroform)

Sources & evidence

ORD record
ord-dd8bee05e2c34f48928e9d659deefb45
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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