1-Methyl-2-imidazolecarboxaldehyde → HCID 46233761、化合物

HRID 1509774ノート

反応式

HRID 1509774 の反応式
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1.[CH3:14][N:15]1[CH:19]=[CH:18][N:17]=[C:16]1[CH:20]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[C:36]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])(=[O:39])[CH:37]=O>ClCCCl.CC(O)=O>[CH3:14][N:15]1[CH:19]=[CH:18][N:17]=[C:16]1[CH2:20][N:1]([CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([S:10](=[O:11])(=[O:12])[NH2:13])=[CH:8][CH:9]=1)[CH2:37][C:36]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39]

参加物

7

反応物 4

HCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 1696824-(2-Aminoethyl)benzenesulfonamideHCID 5049666Sodium triacetoxyborohydrideHCID 10986247Tert-butyl 2-oxoacetate

生成物 1

HCID 46233761HCID 46233761、化合物

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 176Acetic Acid溶媒

反応条件

温度
0 °C

実験手順

A solution of 4-(2-aminoethyl)benzenesulfonamide (1.40 g, 7.0 mmol), AcOH (0.30 mL) and 1-methyl-1H-imidazole-2-carboxaldehyde (0.77 g, 7.0 mmol) in DCE (40 mL) was heated at 80° C. for 30 min under nitrogen. The reaction mixture was cooled to 0° C., and treated sequentially with NaBH(OAc)3 (4.45 g, 21 mmol) and tert-butyl glyoxalate (1.80 g). The reaction mixture was stirred at room temperature overnight and quenched with water. The reaction mixture was then extracted with DCM and the organic layer was dried and concentrated under reduced pressure. The residue obtained was purified by flash chromatography over silica gel to tert-butyl 2-(((1-methyl-1H-imidazol-2-yl)methyl)(4-sulfamoylphenethyl)amino)acetate (0.63 g, 22%). 1H NMR (400 MHz, DMSO-d6) δ 7.65 (d, J=8.4 Hz, 2 H), 7.26 (s, 2 H), 7.21 (d, J=8.0 Hz, 2 H), 6.99 (d, J=0.8 Hz, 1 H), 6.73 (d, J=0.8 Hz, 1 H), 3.76 (s, 2 H), 3.38 (s, 3 H), 3.28 (s, 2 H), 2.79 (t, J=7.2 Hz, 2 H), 2.69 (t, J=6.8 Hz, 2 H), 1.40 (s, 9 H); ESMS m/z: 409 (M+H)+.

後処理

  1. customquenched with water
  2. extractionThe reaction mixture was then extracted with DCM
  3. customthe organic layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customwas purified by flash chromatography over silica gel to tert-butyl 2-(((1-methyl-1H-imidazol-2-yl)methyl)(4-sulfamoylphenethyl)amino)acetate (0.63 g, 22%)

出典と根拠

ORDレコード
ord-6dc895a289b44da4beb4c5e2b23bb9e2
出典データセット
uspto-grants-2012_07
特許番号
US08211402B2

反応ノート

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