1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 69421660, compound

HRID 1349780Notes

Reaction equation

HRID 1349780 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14](C#N)[CH:15]=3)[N:10]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:25]([O:28][C@@H:29]([CH3:33])[C:30](O)=[O:31])(=[O:27])[CH3:26].Cl.[CH3:35][N:36](C)CCCN=C=NCC>ClCCl>[C:25]([O:28][C@H:29]([C:30](=[O:31])[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH:19]3[CH2:24][CH2:23][CH:22]([C:35]#[N:36])[CH2:21][O:20]3)[N:9]=2)[CH:3]=1)[CH3:33])(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 6326324(2S)-2-(Acetyloxy)propanoic acidHCID 22480146HCID 22480146, compound

Product 1

HCID 69421660HCID 69421660, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3-aminophenyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (0.400 g, 1.25 mmol) in dichloromethane (50 mL), was added (S)-(−)-2-acetoxy propionic acid (0.128 mL, 1.38 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDCI) (0.287 g, 1.5 mmol). After overnight reaction at room temperature, 0.6 equivalent of carboxylic acid and EDCI were added. After 12 hours at room temperature, the reaction was complete. The reaction mixture was partitioned between dichloromethane and water. The organic phase was dried under vacuum and the title product was used in the subsequent step without further purification (0.460 g, 85% yield): ES-MS (m/z) 433 [M+H]+.

Workup

  1. customAfter overnight reaction at room temperature
  2. customThe reaction mixture was partitioned between dichloromethane and water
  3. customThe organic phase was dried under vacuum
  4. customthe title product was used in the subsequent step without further purification (0.460 g, 85% yield)

Sources & evidence

ORD record
ord-5c2ab9259c444ac7b515e9c179892796
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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