2-Methoxyethylamine → HCID 69892592, compound

HRID 48352Notes

Reaction equation

HRID 48352 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH:5]=[CH:6][C:7]1=[N:8][CH2:9][CH2:10][N:11]([CH2:18][C:19]([OH:21])=O)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]1=2.[ClH:26].CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[CH3:49][O:50][CH2:51][CH2:52][NH2:53]>ClCCl>[ClH:1].[ClH:26].[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH:5]=[CH:6][C:7]1=[N:8][CH2:9][CH2:10][N:11]([CH2:18][C:19]([NH:53][CH2:52][CH2:51][O:50][CH3:49])=[O:21])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]1=2

Participants

6

Reactant 4

HCID 80182-MethoxyethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69892105(E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1H-1,4-benzodiazepine-1-acetic acid

Product 1

HCID 69892592HCID 69892592, compoundYield 22.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 33 mg (0.088 mmol) of (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1H-1,4-benzodiazepine-1-acetic acid, 30 mg (0.157 mmol) of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride, 16 mg (0.105 mmol) of 1-hydroxybenzotriazole hydrate and 14 mg (0.187 mmol) of 2-methoxyethylamine was stirred in 3 ml of dichloromethane for 3 hours. The solution was washed with saturated sodium bicarbonate solution, dried over magnesium sulphate, filtered and evaporated to dryness. The residue was chromatographed three times on silica gel using dichloromethane/methanol (94:6), dichloromethane/methanol 92:8) and ethyl acetate/methanol (9:1) for the elutions. The product was dissolved in a solution of hydrogen chloride in ethyl acetate, evaporated to dryness and the residue triturated with diethyl ether. There was obtained 5 mg of (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-N-(2-methoxyethyl)-1H-1,4-benzodiazepin-1-acetamide dihydrochloride as a red solid. MS: m/e 431.9 [M+H]+.

Workup

  1. washThe solution was washed with saturated sodium bicarbonate solution
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was chromatographed three times on silica gel
  6. dissolutionThe product was dissolved in a solution of hydrogen chloride in ethyl acetate
  7. customevaporated to dryness
  8. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-e11089c136ae486ab43fbbec7a24bff8
Source dataset
uspto-grants-2004_03
Patent number
US06703387B2

Reaction notes

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