1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 131730985, compound

HRID 2035518Notes

Reaction equation

HRID 2035518 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[CH:13][C:12]([CH2:15][C:16]([NH2:18])=[O:17])=[C:11]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:10]=2)=[CH:4][CH:3]=1.[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][CH2:37][CH:36]([C:40](O)=[O:41])[CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28].Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[CH2:20]([NH:19][C:11]1[CH:10]=[C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:40]([C:36]3[CH2:35][N:34]([C:32]([O:31][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:33])[CH:39]=[CH:38][CH:37]=3)=[O:41])=[CH:7][CH:6]=2)[N:14]=[CH:13][C:12]=1[CH2:15][C:16]([NH2:18])=[O:17])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acidHCID 131730943HCID 131730943, compound

Product 1

HCID 131730985HCID 131730985, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

30 mg of 6-[(4-aminophenyl)amino]-4-(benzylamino) pyridine-3-carboxyamide (the compound of Example 65) was dissolved in 2 mL of methylene chloride, to which 25 mg of 1-(tert-butoxycarbonyl)-3-piperidine carboxylic acid, 21 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 13 mg of N,N-dimethylaminopyridine were added, and stirred overnight at room temperature. The reaction mixture was washed with water, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel thin layer chromatography (chloroform:methanol) to obtain 38 mg (78%) of the title compound as a light pink crystalline powder.

Workup

  1. additionwere added
  2. washThe reaction mixture was washed with water
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel thin layer chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-d8d3238006714c41aecea081559ef48d
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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