Cyclopropanecarbonyl chloride → Cyclopropanecarboxylic acid [2-(2-methoxy-benzylamino)-quinolin-6-yl]-amide

HRID 1803084Notes

Reaction equation

HRID 1803084 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][NH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH2:17])[CH:13]=2)[N:8]=1.[CH:22]1([C:25](Cl)=[O:26])[CH2:24][CH2:23]1>C(#N)C.C(=O)(O)[O-].[Na+].O>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][NH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:17][C:25]([CH:22]3[CH2:24][CH2:23]3)=[O:26])[CH:13]=2)[N:8]=1

Participants

6

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 43450845N2-(2-Methoxy-benzyl)-quinoline-2,6-diamine

Product 1

HCID 44223161Cyclopropanecarboxylic acid [2-(2-methoxy-benzylamino)-quinolin-6-yl]-amide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Procedure

N2-(2-Methoxy-benzyl)-quinoline-2,6-diamine (example 10, step B, 150 mg, 0.537 mmol) was dissolved in 6 mL acetonitrile and 6 mL saturated sodium bicarbonate solution. Cyclopropane carbonyl chloride (63 mg, 0.60 mmol) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with 50 mL water and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with water (30 ml), dried with sodium sulfate and evaporated. The crude product was recrystallized from diisopropyl ether. The title compound was obtained as a white solid (123 mg, 66%), MS: m/e=348.3 (M+H+).

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. washThe combined organic layers were washed with water (30 ml)
  3. dry with materialdried with sodium sulfate
  4. customevaporated
  5. customThe crude product was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-b43b41d1067a4f989da324ea04306c4e
Source dataset
uspto-grants-2013_01
Patent number
US08350028B2

Reaction notes

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