Triethylamine → HCID 11952516, compound

HRID 548602Notes

Reaction equation

HRID 548602 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].Cl.Cl.[NH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH:16][C:17]2[N:18]([CH2:31][CH2:32][CH3:33])[N:19]=[C:20]3[C:29]=2[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N:22]=[C:21]3[NH2:30])[CH2:10][CH2:9]1.C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][NH:16][C:17]2[N:18]([CH2:31][CH2:32][CH3:33])[N:19]=[C:20]3[C:29]=2[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N:22]=[C:21]3[NH2:30])[CH2:12][CH2:13]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 86630221HCID 86630221, compound

Product 1

HCID 11952516HCID 11952516, compoundYield 16.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (0.30 g, 0.20 mL, 2.58 mmol) was added to a stirring suspension of N1-(2-piperidin-4-ylethyl)-2-propyl-2H-pyrazolo[3,4-c]quinoline-1,4-diamine dihydrochloride (1.0 g, 2.35 mmol) and triethylamine (0.59 g, 0.82 mL, 5.88 mmol) in dichloromethane (10 mL). The resulting suspension was stirred at ambient temperature 16 hours. Additional dichloromethane (90 mL), triethylamine (4.2 g, 5.7 mL, 41.1 mmol) and methanesulfonyl chloride (0.19 g, 0.13 mL, 1.66 mmol) were added to the mixture and the resulting cloudy suspension was stirred at ambient temperature 3 days. The reaction mixture was concentrated and the resulting brown solid was purified by column chromatography using a HORIZON HPFC system (silica cartridge, eluting with 5-20% methanol in dichloromethane). The resulting oil was crystallized from acetonitrile and isolated by filtration to yield 169 mg of N1-{2-[1-(methylsulfonyl)piperidin-4-yl]ethyl}-2-propyl-2H-pyrazolo[3,4-c]quinoline-1,4-diamine as an off-white solid, mp 204-207° C. Anal. calcd for C21H30N6O2S: C, 58.58; H, 7.02; N, 19.52. Found: C, 58.77; H, 6.92; N, 19.54.

Workup

  1. stirringthe resulting cloudy suspension was stirred at ambient temperature 3 days
  2. concentrationThe reaction mixture was concentrated
  3. customthe resulting brown solid was purified by column chromatography
  4. washa HORIZON HPFC system (silica cartridge, eluting with 5-20% methanol in dichloromethane)
  5. customThe resulting oil was crystallized from acetonitrile
  6. customisolated by filtration

Sources & evidence

ORD record
ord-b0eeba48cd9d4036919117a226580f1c
Source dataset
uspto-grants-2011_05
Patent number
US07943610B2

Reaction notes

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