Water → N-(6-chloro-7-ethylsulfanyl-9H-beta-carbolin-8-yl)-2-methyl-nicotinamide

HRID 12203

Reaction equation

HRID 12203 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:18])[C:14]=1[S:15][CH2:16][CH3:17])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.[CH3:19][C:20]1[N:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](O)=[O:23].Cl.CN(C)CCCN=C=NCC.O>N1C=CC=CC=1.CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:18][C:22](=[O:23])[C:21]3[CH:25]=[CH:26][CH:27]=[N:28][C:20]=3[CH3:19])[C:14]=1[S:15][CH2:16][CH3:17])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Participants

7

Reactant 4

HCID 962WaterHCID 6433732-Methylnicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 671665956-chloro-7-ethylsulfanyl-9H-beta-carbolin-8-ylamine

Product 1

HCID 11280944N-(6-chloro-7-ethylsulfanyl-9H-beta-carbolin-8-yl)-2-methyl-nicotinamideYield 40.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

A 25 ml round-bottom flask with magnetic stirrer was charged with 6-chloro-7-ethylsulfanyl-9H-β-carbolin-8-ylamine (37.2 mg, 0.13 mmol) and 2-methylnicotinic acid (36.2 mg, 0.26 mmol) in 3 ml anhydrous pyridine. To the resulting light-orange mixture at RT was added solid 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (73.2 mg, 0.38 mmol) and the resulting reaction mixture was heated to 80° C. for 5 days. Next, the reaction mixture was cooled to RT and concentrated to afford a brown, viscous syrup. The syrup was dissolved in a minimal amount of MeOH (˜2 ml), slowly added to a 5:1 mixture of H2O/saturated sodium bicarbonate (˜20 ml), and stirred at RT for 2.5 hr. The resulting precipitated solid was collected via suction filtration, washed with 1:1 hexanes/diethyl ether (2×20 ml), and air-dried to afford 21.0 mg of N-(6-chloro-7-ethylsulfanyl-9H-β-carbolin-8-yl)-2-methyl-nicotinamide as a tan solid (˜38%). LCMS (ammonium acetate standard method) retention time=2.33 min. (M+=397; M−=395).

Workup

  1. customthe resulting reaction mixture
  2. temperatureNext, the reaction mixture was cooled to RT
  3. concentrationconcentrated
  4. customto afford a brown, viscous syrup
  5. customThe resulting precipitated solid
  6. filtrationwas collected via suction filtration
  7. washwashed with 1:1 hexanes/diethyl ether (2×20 ml)
  8. customair-dried

Sources & evidence

ORD record
ord-44615147f6f746779af7e52873f60a22
Source dataset
uspto-grants-2010_06
Patent number
US07727985B2

Linked notes

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