Triethylamine → HCID 178505297, compound

HRID 2271552Notes

Reaction equation

HRID 2271552 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[NH:17][C@H:18]1[CH2:23][CH2:22][C@H:21]([CH2:24][OH:25])[CH2:20][CH2:19]1.C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>ClCCl.C(=O)(O)[O-].[Na+]>[CH3:33][S:34]([O:25][CH2:24][C@H:21]1[CH2:22][CH2:23][C@H:18]([NH:17][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])[CH2:19][CH2:20]1)(=[O:36])=[O:35]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178519795HCID 178519795, compound

Product 1

HCID 178505297HCID 178505297, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a suspension of (6-bromo-4-((trans-4-(hydroxymethyl)cyclohexyl)amino)quinolin-3-yl) (cyclopropyl)methanone (1.23 g, 3.05 mmol) in dichloromethane (60 mL) was added triethylamine (2.09 mL, 15 mmol) and methanesulfonyl chloride (0.35 mL, 4.5 mmol) was added dropwise. The reaction mixture was stirred for 2 h. The solution was then diluted with saturated sodium bicarbonate solution and extracted with dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated. Purification by column chromatography (silica, ethyl acteate/hexanes) afforded the desired product (0.98 g, 67%) as a white solid. ESI MS m/z 481 [C21H25BrN2O4S+H]+

Workup

  1. additionwas added dropwise
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customPurification by column chromatography (silica, ethyl acteate/hexanes)

Sources & evidence

ORD record
ord-499b022011df4caa89c0f2a8719130f8
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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