1,2-Ethanediamine, N1,N1,N2-trimethyl- → HCID 178483773, compound

HRID 2240087Notes

Reaction equation

HRID 2240087 reaction equation
[C:1]1([S:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([CH:23]=O)[CH:21]=3)[NH:16][N:15]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:25][NH:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH3:30][N:29]([CH3:31])[CH2:28][CH2:27][N:26]([CH3:25])[CH2:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[NH:16][N:15]=[C:14]2[S:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 5049666Sodium triacetoxyborohydrideHCID 178519381HCID 178519381, compound

Product 1

HCID 178483773HCID 178483773, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

3-(Naphthalene-1-sulfonyl)-1H-indazole-5-carbaldehyde (0.17 g, 0.5 mmol), trimethyl ethylene diamine (0.6 mmol) and sodium triacetoxyborohydride (0.7 mmol) in dichloroethane (5 mL) was stirred at room temperature for 24 hrs. After completion, the solvent was removed in vacuo, crude material dispersed in water and the pH brought to 3.4. Solid material was filtered off and washed with cold water to afford after drying the target material as a free base. The latter was converted into hydrochloride salt by dissolution in methanol, followed by treatment with the excess of 2N HCl and the evacuation of the volatiles in vacuo to afford the title compound hydrochloride salt, mp>200° C.; MS (APPI) 423 [M+H]

Workup

  1. customAfter completion, the solvent was removed in vacuo, crude material
  2. additiondispersed in water
  3. filtrationSolid material was filtered off
  4. washwashed with cold water
  5. customto afford
  6. customafter drying the target material as a free base
  7. dissolutionThe latter was converted into hydrochloride salt by dissolution in methanol

Sources & evidence

ORD record
ord-839bd9f1f85e49fc81ae8722a8caa665
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

Loading…