1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 131731010, compound

HRID 2035550Notes

Reaction equation

HRID 2035550 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([N:15]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[C:16]2[CH:17]=[N:18][C:19]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:20][CH:21]=2)[N:12]=[CH:11][C:10]=1C(O)=O)C1C=CC=CC=1.Cl.[CH2:41]([N:43]=C=NCCCN(C)C)[CH3:42].[OH2:52].ON1[C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][C:57]=2N=N1.O.N>ClCCl.O>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([N:15]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[C:16]2[CH:17]=[N:18][C:19]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:20][CH:21]=2)[N:12]=[CH:11][C:10]=1[CH2:42][C:41]([NH2:43])=[O:52])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 12896473Azane;hydrateHCID 674139734-Benzylamino-6-[4-methoxybenzyl-(6-morpholinopyridin-3-yl)amino]pyridine-3-carboxylic acid

Product 1

HCID 131731010HCID 131731010, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3.4 mg of 4-benzylamino-6-[4-methoxybenzyl-(6-morpholinopyridin-3-yl)amino]pyridine-3-carboxylic acid was dissolved in 1 mL of dichloromethane, to which 1.9 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 1.5 mg of 1-hydroxybenzotriazole monohydrate were added, and stirred at room temperature for 30 minutes. Then, 1 mL of 28% ammonia water was added, and stirred at the same temperature for 3 hours. To the reaction mixture water was added, extracted with chloroform, the extract was washed with saturated saline, and dried on anhydrous sodium sulfate. The solvent was evaporated to obtain 3.0 mg of the title compound containing impurities as a brown solid. Without further purification, this was used in the next reaction as it was.

Workup

  1. additionwere added
  2. stirringstirred at the same temperature for 3 hours
  3. extractionextracted with chloroform
  4. washthe extract was washed with saturated saline
  5. dry with materialdried on anhydrous sodium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-747b026ed676487c8e2dfc62e2928c1c
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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