p-Toluenesulfonic acid → HCID 59447948, compound

HRID 1916288Notes

Reaction equation

HRID 1916288 reaction equation
Cl[C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([C:15]#[N:16])=[CH:11][CH:12]=3)[NH:7][C:6]=2[N:5]=[CH:4][N:3]=1.[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20][NH2:21].C(N(C(C)C)C(C)C)C.CC1C=CC(S(O)(=O)=O)=CC=1>CN1C(=O)CCC1.CO>[CH3:17][N:18]([CH3:22])[CH2:19][CH2:20][NH:21][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([C:15]#[N:16])=[CH:11][CH:12]=3)[NH:7][C:6]=2[N:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 59447941HCID 59447941, compound

Product 1

HCID 59447948HCID 59447948, compoundYield 18.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-chloro-9H-pyrimido[4,5-b]indole-7-carbonitrile (23 mg, 0.10 mmol), 2-dimethylaminoethylamine (27 mg, 0.3 mmol) and N-ethyldiisopropylamine (88 μL, 0.50 mmol) in 1 ml of NMP was heated at 140° C. for 20 minutes using microwave irradiation. The reaction mixture was diluted with 5 mL methanol and applied to a 500 mg MP-TsOH SPE cartridge. After washing the cartridge, the product was eluted using 2 N ammonia in methanol. The eluent was concentrated in vacuo and the residue purified by prep HPLC to give 5.1 mg of the title compound as a white solid. 1H NMR (DMSO, δ, ppm) δ 2.3 (6H, s), 2.65 (2H, t, J=6.8 Hz), 3.7-3.8 (2H, m), 7.45 (1H, t, J=6.1 Hz), 7.7 (1H, d, J=8.1 Hz), 7.9 (1H, s), 8.2 (1H, s), 8.4 (1H, s), 8.5 (1H, d, J=8.1 Hz), 12.4 (1H, br s); LC-MS (2) Rt 2.03 min; m/z (ES+) 281.

Workup

  1. custommicrowave irradiation
  2. washAfter washing the cartridge
  3. washthe product was eluted
  4. concentrationThe eluent was concentrated in vacuo
  5. customthe residue purified by prep HPLC

Sources & evidence

ORD record
ord-3f03e4dd976d4441b74021f1b8fd2ba9
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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