Triethylamine → 3-(3-chlorophenyl)-N-(2,4-dimethoxybenzyl)-2-oxo-N-(1,3,4-thiadiazol-2-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide

HRID 528567

反応式

HRID 528567 の反応式
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.[CH3:11][O:12][C:13]1[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:14]=1[CH2:15][N:16]([C:30]1[S:31][CH:32]=[N:33][N:34]=1)[S:17]([C:20]1[CH:29]=[CH:28][C:23]2[NH:24][C:25](=[O:27])[O:26][C:22]=2[CH:21]=1)(=[O:19])=[O:18].C(N(CC)CC)C.[NH4+].[OH-]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CCOC(C)=O.O.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:24]2[C:23]3[CH:28]=[CH:29][C:20]([S:17]([N:16]([CH2:15][C:14]4[CH:35]=[CH:36][C:37]([O:39][CH3:40])=[CH:38][C:13]=4[O:12][CH3:11])[C:30]4[S:31][CH:32]=[N:33][N:34]=4)(=[O:19])=[O:18])=[CH:21][C:22]=3[O:26][C:25]2=[O:27])[CH:5]=[CH:6][CH:7]=1

参加物

9

反応物 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 2734323(3-Chlorophenyl)boronic acidHCID 89761668N-(2,4-dimethoxybenzyl)-2-oxo-N-(1,3,4-thiadiazol-2-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide

生成物 1

HCID 897613473-(3-chlorophenyl)-N-(2,4-dimethoxybenzyl)-2-oxo-N-(1,3,4-thiadiazol-2-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide収率 62.4%

試薬・触媒・溶媒 4

HCID 8895Cupric acetate触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

A sealable vial was charged with (3-chlorophenyl)boronic acid (25.6 mg, 0.164 mmol), N-(2,4-dimethoxybenzyl)-2-oxo-N-(1,3,4-thiadiazol-2-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide (48.9 mg, 0.109 mmol), 3 Å molecular sieves (powdered, 60 mg), DCM (545 μl), and triethylamine (45.6 μl, 0.327 mmol). Copper (II) acetate (39.6 mg, 0.218 mmol) was added as a solid in a single portion. The mixture was stirred at rt for 48 h. The reaction mixture was poured into a mixture of NH4OH and water (10% NH4OH in H2O), extracted with DCM (2×10 mL), organic layers (which were an emulsion) were combined and washed with water (10 mL) then brine (20 mL), the emulsion resolved upon brine wash. The organic layers were dried (Na2SO4) and concentrated for purification by silica gel MPLC. The residue was taken up in minimal DCM and absorbed onto a 5 g loading cartridge and passed through a silica gel column (12 g) using 98:2 Heptane:EtOAc to 100% EtOAc gradient to afford 3-(3-chlorophenyl)-N-(2,4-dimethoxybenzyl)-2-oxo-N-(1,3,4-thiadiazol-2-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide (38.0 mg, 0.068 mmol) as a white amorphous solid. m/z (ESI) 559.2 (M+H)+.

後処理

  1. extractionextracted with DCM (2×10 mL), organic layers (which
  2. washwashed with water (10 mL)
  3. washwash
  4. dry with materialThe organic layers were dried (Na2SO4)
  5. concentrationconcentrated for purification by silica gel MPLC
  6. customabsorbed onto a 5 g loading cartridge

出典と根拠

ORDレコード
ord-b99a9845c1b74e5aa7069019eabcf636
出典データセット
uspto-grants-2016_05
特許番号
US09346798B2

関連ノート

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