Dimethylamine → HCID 71186206、化合物

HRID 1470511ノート

反応式

HRID 1470511 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12](O)=[O:13])=[CH:9][CH:8]=[C:7]2[O:15][CH3:16].O=S(Cl)Cl.C[CH2:22][N:23](C(C)C)[CH:24](C)C.CNC>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12]([N:23]([CH3:24])[CH3:22])=[O:13])=[CH:9][CH:8]=[C:7]2[O:15][CH3:16]

参加物

6

反応物 4

HCID 674DimethylamineHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 71185803HCID 71185803、化合物

生成物 1

HCID 71186206HCID 71186206、化合物収率 95%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 8-chloro-4-methoxy-1-naphthoic acid (step-4 intermediate) (0.5 g, 2.11 mmol) in CH2Cl2 (5 mL) was added, SOCl2 (0.31 mL, 4.22 mmol, 2.0 eq.) and the mixture was stirred at RT for 3 h. The solvent was evaporated under reduced pressure and the crude product was dissolved in DCM (10 mL). To this, DIPEA (0.74 mL, 4.23 mmol) was added followed by dimethylamine (1.5 eq.) and the reaction mixture was stirred at RT for 3 h and then quenched with ice. The aqueous layer was extracted with dichloromethane and the combined organic layer was washed with sat. NaHCO3 solution, water, brine, dried over Na2SO4 and filtered. The solvent was evaporated to provide the desired amide derivative (528 mg, 95%) this was used in the next step without any further purification.

後処理

  1. additionwas added
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe crude product was dissolved in DCM (10 mL)
  4. customquenched with ice
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. washthe combined organic layer was washed with sat. NaHCO3 solution, water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-5e4f5121cba14064a662525ce0cfd321
出典データセット
uspto-grants-2015_04
特許番号
US09006442B2

反応ノート

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