Triethylamine → HCID 178468889, compound

HRID 219439Notes

Reaction equation

HRID 219439 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][CH2:10][C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][C:12]=2[NH:22][C:23](=[O:38])[C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:36][CH2:35][CH2:34][N:33]([CH3:37])[CH2:32][CH2:31]3)=[CH:26][CH:25]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].Cl.[NH2:40][OH:41].C(N(CC)CC)C>C(O)C>[OH:41][NH:40][C:1]([C:3]1[CH:4]=[C:5]([NH:9][CH2:10][C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][C:12]=2[NH:22][C:23](=[O:38])[C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:36][CH2:35][CH2:34][N:33]([CH3:37])[CH2:32][CH2:31]3)=[CH:26][CH:25]=2)[CH:6]=[CH:7][CH:8]=1)=[NH:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 18001108HCID 18001108, compound

Product 1

HCID 178468889HCID 178468889, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 4-[(3-cyanophenylamino)methyl]-3-[4-(4-methyl-1,4-diazepan-1-yl)benzoylamino]benzoate (1.42 g) was dissolved in 30 ml of ethanol, then 291 mg of hydroxylamine hydrochloride and 0.78 ml of triethylamine were added and the mixture was stirred at 60° C. for 24 hours. The reaction solution was concentrated in vacuo and the resulting residue was purified by silica gel column chromatography using chloroform-methanol-aqueous ammonia (100:0:0 to 92:8:0.8) to give a crudely purified product, ethyl 4-([{3-(N-hydroxycarbamimidoyl)phenyl]amino}methyl)-3-[4-(4-methyl-1,4-diazepan-1-yl)benzoylamino]benzoate. The crudely purified product was further purified by ODS column chromatography using 0.002N aqueous solution of hydrochloric acid-methanol (100:0 to 88:12) as an eluting solvent and freeze-dried to give 1.03 g of ethyl 4-([{3-(N-hydroxycarbamimidoyl)phenyl]amino}methyl)-3-[4-(4-methyl-1,4-diazepan-1-yl)benzoylamino]benzoate hydrochloride.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9299dbc1fda8417ba6bb1d34b609071a
Source dataset
uspto-grants-2012_06
Patent number
USRE043481E1

Reaction notes

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