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

HRID 1253936ノート

反応式

HRID 1253936 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178460666HCID 178460666、化合物触媒HCID 1140Toluene溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-633edaea3c4f4799b033a651fa3b9b1c
出典データセット
uspto-grants-2013_06
特許番号
US08455522B2

反応ノート

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