Ethanesulfonamide → N-((5-(3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)pyridin-3-yl)methyl)ethanesulfonamide

HRID 1253936노트

반응식

HRID 1253936 반응식
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([CH:17]=O)[CH:14]=[N:15][CH:16]=3)[CH:9]=[CH:10][C:5]=2[O:4][C:3]1=[O:19].[CH2:20]([S:22]([NH2:25])(=[O:24])=[O:23])[CH3:21].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([CH2:17][NH:25][S:22]([CH2:20][CH3:21])(=[O:24])=[O:23])[CH:14]=[N:15][CH:16]=3)[CH:9]=[CH:10][C:5]=2[O:4][C:3]1=[O:19]

참가 물질

7

반응물 4

HCID 73702EthanesulfonamideHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 866633595-(3-Methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-pyridine-3-carbaldehyde

생성물 1

HCID 66798043N-((5-(3-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)pyridin-3-yl)methyl)ethanesulfonamide수율 72%

시약·촉매·용매 2

HCID 178460666HCID 178460666, 화합물촉매HCID 1140Toluene용매

실험 절차

A mixture of 5-(3-Methyl-2-oxo-2,3-dihydro-benzooxazol-5-yl)-pyridine-3-carbaldehyde (51 mg, 0.2 mmol), ethanesulfonamide (33 mg, 0.3 mmol), Ti(OiPr)4 (118 uL, 114 mg, 0.4 mmol) in toluene (5 mL) was heated to reflux for overnight. After concentration, the residue was dissolved into CH2Cl2 (5 mL). NaBH(OAc)3 (127 mg, 0.6 mmol) was added at room temperature. The resulting mixture was stirred for 4 h at this temperature. Saturated NaHCO3 solution was added, and the mixture was extracted with CH2Cl2. The combined extracts were dried over anhydrous Na2SO4. After filteration and concentration, the residue was purified by flash column (MeOH—CH2Cl2, v/v, 1-3.5%) and afforded the title product (50 mg), ESI-MS m/z: 348.0 [M+1]+, Retention time 1.01 min; 1HNMR (CDCl3, 400.342 MHz) δ 1.40 (t, J=7.4 Hz, 3H), 3.07 (q, J=7.4 Hz, 2H), 3.48 (s, 3H), 4.42 (d, J=6 Hz, 2H), 4.60 (t, J=6 Hz, 1H), 7.13 (s, 1H), 7.31 (s, 2H), 7.92 (s, 1H), 8.57 (d, J=14 Hz, 1H), 8.77 (d, J=1.4 Hz, 1H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for overnight
  3. concentrationAfter concentration
  4. dissolutionthe residue was dissolved into CH2Cl2 (5 mL)
  5. extractionthe mixture was extracted with CH2Cl2
  6. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  7. concentrationAfter filteration and concentration
  8. customthe residue was purified by flash column (MeOH—CH2Cl2, v/v, 1-3.5%)

출처 및 근거

ORD 기록
ord-633edaea3c4f4799b033a651fa3b9b1c
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455522B2

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