Triethylamine → HCID 11461687, compound

HRID 1364042Notes

Reaction equation

HRID 1364042 reaction equation
C(N(CC)CC)C.Cl.[CH:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11]1[N:22]3[CH2:23][CH2:24][CH2:25][NH:26][CH2:27][C:21]3=[N:20][C:12]=1[C:13]([NH2:19])=[N:14]2.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>CN(C=O)C>[CH3:28][S:29]([N:26]1[CH2:25][CH2:24][CH2:23][N:22]2[C:11]3[C:10]4[C:15](=[CH:16][CH:17]=[CH:18][CH:9]=4)[N:14]=[C:13]([NH2:19])[C:12]=3[N:20]=[C:21]2[CH2:27]1)(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66958500HCID 66958500, compound

Product 1

HCID 11461687HCID 11461687, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (2.32 mL, 16.7 mmol) was added to a suspension of 9,10,11,12-tetrahydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine hydrochloride (1.61 g, 5.56 mmol, Example 7 Part A) in DMF (20 mL). The mixture was sonicated for ten minutes at 80° C., and methanesulfonyl chloride (764 mg, 6.67 mmol) was slowly added. The mixture was stirred at ambient temperature overnight. The solvent was removed under reduced pressure. Unsuccessful attempts were made to purify the product, and ultimately, the product was isolated by filtration to provide 894 mg of 9-(methylsulfonyl)-9,10,11,12-tetrahydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine containing some impurities.

Workup

  1. customThe mixture was sonicated for ten minutes at 80° C.
  2. customThe solvent was removed under reduced pressure
  3. customto purify the product
  4. customultimately, the product was isolated by filtration

Sources & evidence

ORD record
ord-4e3f98addfa94bd2bc51bd66a7fb3433
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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