Hydrochloric Acid → 3-hydroxy-4-methoxy-N-(4-(4-trifluoromethylphenoxy)phenyl)-pyridine-2-carboxamide

HRID 277163노트

반응식

HRID 277163 반응식
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:16]=[CH:15][C:6]([O:7][C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.Br[C:20]1[N:25]=[C:24]([C:26](Cl)=[O:27])[C:23]([O:29]CC2C=CC=CC=2)=[C:22]([O:37][CH3:38])[CH:21]=1.Cl.C(N(CC)CC)C.[H][H]>CN(C1C=CN=CC=1)C.C(Cl)Cl.CCOC(C)=O.[Pd]>[OH:29][C:23]1[C:24]([C:26]([NH:12][C:11]2[CH:10]=[CH:9][C:8]([O:7][C:6]3[CH:15]=[CH:16][C:3]([C:2]([F:17])([F:18])[F:1])=[CH:4][CH:5]=3)=[CH:14][CH:13]=2)=[O:27])=[N:25][CH:20]=[CH:21][C:22]=1[O:37][CH3:38]

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27607514-(4-(Trifluoromethyl)phenoxy)anilineHCID 221750736-bromo-3-benzyloxy-4-methoxypyridine-2-carbonyl ChlorideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 221751703-hydroxy-4-methoxy-N-(4-(4-trifluoromethylphenoxy)phenyl)-pyridine-2-carboxamide수율 43.3%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 23938Palladium촉매HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 4-(4-trifluoromethylphenoxy) aniline (0.20 g, 0.8 mmol) and DMAP (0.10 g, 0.085 mmol) in CH2Cl2 (10 mL) was added all at once a solution of 3-benzyloxy-6-bromo-4-methoxypyridin-2-carbonylchloride (3) (0.29 g, 0.8 mmol) in CH2Cl2 (5 mL). The resulting mixture was stirred overnight at room temperature then poured into 2N HCl (10 mL). The organic layer was separated and the aqueous layer extracted with CH2Cl2 (2×10 mL). The organic layers were combined, dried (MgSO4) and concentrated to give a gummy solid. This solid was taken up in EtOAc (20 mL), and triethylamine (0.80 g, 0.8 mmol) and 5% Pd on carbon (0.10 g) were added. The resulting mixture was subjected to a hydrogen atmosphere (initial pressure=50 psi) on a Parr shaker for 30 minutes. The mixture was filtered, washed with 0.1N HCl (20 mL), dried (MgSO4) and concentrated to give the title compound as an off-white solid (0.14 g), m.p.=122-129° C.

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted with CH2Cl2 (2×10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give a gummy solid
  6. customfor 30 minutes
  7. filtrationThe mixture was filtered
  8. washwashed with 0.1N HCl (20 mL)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3f83d36b38fb41ce82d6434a11a3918a
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355660B1

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