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

HRID 1830991

반응식

HRID 1830991 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-11852088d3074b6fbabc22a433957904
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067543B2

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