Triethylamine → HCID 57717566, compound

HRID 1984422Notes

Reaction equation

HRID 1984422 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]([CH3:27])([CH3:26])[CH2:8][C:9]1[N:10]([CH2:23][CH2:24][CH3:25])[N:11]=[C:12]2[C:21]=1[C:20]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:14]=[C:13]2[NH2:22].C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[NH2:22][C:13]1[C:12]2=[N:11][N:10]([CH2:23][CH2:24][CH3:25])[C:9]([CH2:8][C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])([CH3:27])[CH3:26])=[C:21]2[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:14]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 57717565HCID 57717565, compound

Product 1

HCID 57717566HCID 57717566, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (232 μL, 3.00 mmol) was added to a 0° C. stirred solution of 1-(2-amino-2-methylpropyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine (prepared as described in Example 64, 892 mg, 3.00 mmol) and triethylamine (627 μL, 4.5 mmol) in dichloromethane (26.7 mL). After 3 hours at 0° C., the solution was stirred for 2 days at ambient temperature. To the solution was added 2 M aqueous sodium carbonate. The mixture was extracted with chloroform four times. The organic layers were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield a white solid. The crude product was purified by IFC (silica gel, elution with 10% CMA in chloroform). The appropriate fractions were combined and concentrated under reduced pressure to provide a white foam that was crystallized from acetonitrile, isolated by filtration, and dried to yield 600 mg of N-[2-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide as a white solid, mp 130-139° C.

Workup

  1. extractionThe mixture was extracted with chloroform four times
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto yield a white solid
  6. customThe crude product was purified by IFC (silica gel, elution with 10% CMA in chloroform)
  7. concentrationconcentrated under reduced pressure
  8. customto provide a white foam that
  9. customwas crystallized from acetonitrile
  10. customisolated by filtration
  11. customdried

Sources & evidence

ORD record
ord-ec3162862f784ae7b842ea812890f6f4
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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