1-Hydroxybenzotriazole → HCID 22467454, compound

HRID 1934653Notes

Reaction equation

HRID 1934653 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][C:12]=2[C:13]([NH:15][CH2:16][C:17]2[CH:25]=[CH:24][C:20]3[O:21][CH2:22][O:23][C:19]=3[CH:18]=2)=[O:14])[CH2:6][CH2:5]1)([OH:3])=O.Cl.C[N:35](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O.N>[C:1]([CH:4]1[CH2:5][CH2:6][CH:7]([NH:10][C:11]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][C:12]=2[C:13]([NH:15][CH2:16][C:17]2[CH:25]=[CH:24][C:20]3[O:21][CH2:22][O:23][C:19]=3[CH:18]=2)=[O:14])[CH2:8][CH2:9]1)(=[O:3])[NH2:35]

Participants

6

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22467519HCID 22467519, compound

Product 1

HCID 22467454HCID 22467454, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 222AmmoniaCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-(4-carboxycyclohexylamino)-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide (80.0 mg), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (52.1 mg), 1-hydroxybenzotriazole (36.7 mg) in dimethylformamide (1 mL) was added 28% ammonia solution (10 drops). After stirring for 15 hours at ambient temperature, the mixture was partitioned between water and ethyl acetate. The separated organic layer was washed with an aqueous saturated sodium bicarbonate solution, water and brine. Then, the resultant was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with 10% methanol in chloroform. The obtained product was triturated with ciisopropyl ether to give 2-(4-carbamoylcyclohexylamino)-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide as yellow powders (60.0 mg).

Workup

  1. customthe mixture was partitioned between water and ethyl acetate
  2. washThe separated organic layer was washed with an aqueous saturated sodium bicarbonate solution, water and brine
  3. dry with materialThen, the resultant was dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by a silica gel column chromatography
  6. washeluting with 10% methanol in chloroform
  7. customThe obtained product was triturated with ciisopropyl ether

Sources & evidence

ORD record
ord-ed01a9344acf45d5b074a467560d3e7d
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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