Sodium Bicarbonate → 2-[[6-Methoxy-3-pyridinyl]methyl]amino-N-[4-bromo-3-(trifluoromethyl)phenyl]benzamide

HRID 1830991

反応式

HRID 1830991 の反応式
C([BH3-])#N.[Na+].[CH3:5][O:6][C:7]1[N:12]=[CH:11][C:10]([CH:13]=O)=[CH:9][CH:8]=1.[NH2:15][C:16]1[CH:35]=[CH:34][CH:33]=[CH:32][C:17]=1[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=1)=[O:19].C(=O)([O-])O.[Na+]>CO.C(O)(=O)C>[CH3:5][O:6][C:7]1[N:12]=[CH:11][C:10]([CH2:13][NH:15][C:16]2[CH:35]=[CH:34][CH:33]=[CH:32][C:17]=2[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([Br:27])=[C:23]([C:28]([F:31])([F:29])[F:30])[CH:22]=2)=[O:19])=[CH:9][CH:8]=1

参加物

7

反応物 4

HCID 516892Sodium BicarbonateHCID 33645766-Methoxypyridine-3-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 112683582-Amino-N-(4-bromo-3-trifluoromethylphenyl)benzamide

生成物 1

HCID 99130292-[[6-Methoxy-3-pyridinyl]methyl]amino-N-[4-bromo-3-(trifluoromethyl)phenyl]benzamide

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

Sodium cyanoborohydride (8.80 g of 95%, 133 mmol) is added in portions over 30 minutes to a stirred mixture of acetic acid (3.8 mL), 6-methoxy-3-pyridinecarboxaldehyde (Fluka, Buchs, Switzerland; 7.80 g, 57 mmol) and 2-amino-N-(4-bromo-3-trifluoromethylphenyl)benzamide (step 1.2; 13.65 g, 38 mmol) in methanol (380 mL) at 25° C. The mixture is stirred for 16 hours. The solvent is evaporated under reduced pressure to give a residue which is treated with a saturated aqueous solution of sodium hydrogen carbonate (500 mL) and extracted with dichloromethane (3×150 mL). The combined extracts are dried (Na2SO4), filtered and the solvent is evaporated under reduced pressure to yield the crude product that is purified by column chromatography on silica gel, eluent 5% EtOAc in dichloromethane and recrystallised from diethylether-hexane to give the title compound as a beige crystalline solid, m.p. 101–103° C.

後処理

  1. customThe solvent is evaporated under reduced pressure
  2. customto give a residue which
  3. extractionextracted with dichloromethane (3×150 mL)
  4. dry with materialThe combined extracts are dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent is evaporated under reduced pressure
  7. customto yield the crude product that
  8. customis purified by column chromatography on silica gel, eluent 5% EtOAc in dichloromethane
  9. customrecrystallised from diethylether-hexane

出典と根拠

ORDレコード
ord-11852088d3074b6fbabc22a433957904
出典データセット
uspto-grants-2006_06
特許番号
US07067543B2

関連ノート

読み込み中…