1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 18791668, compound

HRID 1005603Notes

Reaction equation

HRID 1005603 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:49]=[CH:48][CH:47]=[CH:46][C:14]=1[C:15]([NH:17][C:18]1[CH:43]=[CH:42][C:21]([C:22]([N:24]([CH3:41])[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=2[O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([OH:40])=[O:39])=[O:23])=[CH:20][C:19]=1[O:44][CH3:45])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(N=C=NC[CH2:57][CH2:58][N:59]([CH3:61])[CH3:60])C>CN(C)C1C=CN=CC=1.ClCCl.C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:49]=[CH:48][CH:47]=[CH:46][C:14]=1[C:15]([NH:17][C:18]1[CH:43]=[CH:42][C:21]([C:22]([N:24]([CH3:41])[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=2[O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH2:57][CH2:58][N:59]([CH3:61])[CH3:60])=[O:39])=[O:23])=[CH:20][C:19]=1[O:44][CH3:45])=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18791200HCID 18791200, compound

Product 1

HCID 18791668HCID 18791668, compoundYield 86.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-[2-(3-tert-butoxycarbonylaminoprop-1-yl)oxybenzoyl]amino-3-methoxy-N-methyl-N-[2-[5-carboxypent-1-yl]oxy-4-methylphenyl]benzamide (250 mg), 2-dimethylaminoethyl (99 mg) and 4-dimethylaminopyridine (36 mg) in dichloromethane (10 ml) was added N-ethyl-N'-(3-dimethylaminoprop-1-yl)carbodiimide hydrochloride (71 mg) at 0° C. and stirred at the same temperature for 7 hours. The mixture was diluted with chloroform (20 ml) and the solution was washed with water (20 ml×2) and brine. The solution was dried over magnesium sulfate and the solvent was removed under reduced pressure. This residue was purified by silica gel column chromatography (SiO2 30 g, 1-10% methanol in chloroform) to give 4-[2-(3-tert-butoxycarbonylaminoprop-1-yl)oxybenzoyl]amino-3-methoxy-N-methyl-N-[2-[5-(2-dimethylaminoeth-1-yl)oxycarbonylpent-1-yl]oxy-4-methylphenyl]benzamide (238 mg).

Workup

  1. washthe solution was washed with water (20 ml×2) and brine
  2. dry with materialThe solution was dried over magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThis residue was purified by silica gel column chromatography (SiO2 30 g, 1-10% methanol in chloroform)

Sources & evidence

ORD record
ord-f13c9058d6274e2bb06cc93844834cad
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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