N,N-Dimethylethylenediamine → HCID 57742591, compound

HRID 1806134Notes

Reaction equation

HRID 1806134 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:18][C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22](O)=[O:23])[C:5]([NH:8][C:9]2[S:10][C:11]3[C:16]([N:17]=2)=[CH:15][CH:14]=[CH:13][N:12]=3)=[N:6][CH:7]=1.[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31][NH2:32].Cl.CN(C)CCCN=C=NCC.C1C=CC2N(O)N=NC=2C=1.O.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([S:18][C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22]([NH:32][CH2:31][CH2:30][N:29]([CH3:33])[CH3:28])=[O:23])[C:5]([NH:8][C:9]2[S:10][C:11]3[C:16]([N:17]=2)=[CH:15][CH:14]=[CH:13][N:12]=3)=[N:6][CH:7]=1

Participants

8

Reactant 5

HCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 57742554HCID 57742554, compound

Product 1

HCID 57742591HCID 57742591, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-(5-bromo-2-(thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)benzoic acid (0.080 g, 0.17 mmol) and N1,N1-dimethylethane-1,2-diamine (0.020 g, 0.23 mmol) were dissolved in DMF. 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.037 g, 0.19 mmol) and HOBT-H2O (0.029 g, 0.19 mmol) were then added. N,N-Diisopropylethylamine (0.034 mL, 0.19 mmol) was added last. The reaction was stirred at ambient temperature for 2 days. The material was diluted with water and the solid was filtered and recrystallized in EtOAc/hexanes to afford the title compound (0.030 g, 33% yield) as a white solid. 1H NMR (CDCl3) δ 2.25 (s, 6H), 2.50 (t, 2H), 3.46-3.51 (m, 2H), 6.91 (bs, 1H), 7.28-7.37 (m, 3H), 7.62 (d, 1H), 7.68 (s, 1H), 7.86 (d, 1H), 7.97 (s, 1H), 8.41 (d, 1H), 8.48 (s, 1H).

Workup

  1. filtrationthe solid was filtered
  2. customrecrystallized in EtOAc/hexanes

Sources & evidence

ORD record
ord-6368e8a3014d4d6ca387a7da1579bc1d
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

Loading…