Acetaldehyde → 4-(4-chloro-2-(1-(1-ethylazetidin-3-yl)-1H-pyrazol-5-yl)phenoxy)-3-cyano-N-(thiazol-4-yl)benzenesulfonaMide

HRID 1401928ノート

反応式

HRID 1401928 の反応式
[NH:1]1[CH2:4][CH:3]([N:5]2[C:9]([C:10]3[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:11]=3[O:12][C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH:22][C:23]4[N:24]=[CH:25][S:26][CH:27]=4)(=[O:21])=[O:20])=[CH:15][C:14]=3[C:28]#[N:29])=[CH:8][CH:7]=[N:6]2)[CH2:2]1.[CH2:35](N(CC)CC)[CH3:36].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)C>CO.ClCCl>[Cl:34][C:32]1[CH:31]=[CH:30][C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([NH:22][C:23]3[N:24]=[CH:25][S:26][CH:27]=3)(=[O:21])=[O:20])=[CH:15][C:14]=2[C:28]#[N:29])=[C:10]([C:9]2[N:5]([CH:3]3[CH2:2][N:1]([CH2:35][CH3:36])[CH2:4]3)[N:6]=[CH:7][CH:8]=2)[CH:33]=1

参加物

7

反応物 4

HCID 177AcetaldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 574948254-[2-(1-azetidin-3-yl-1H-pyrazol-5-yl)-4-chlorophenoxy]-3-cyano-N-1,3-thiazol-4-ylbenzenesulfonamide

生成物 1

HCID 468416484-(4-chloro-2-(1-(1-ethylazetidin-3-yl)-1H-pyrazol-5-yl)phenoxy)-3-cyano-N-(thiazol-4-yl)benzenesulfonaMide

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a suspension of 4-[2-(1-azetidin-3-yl-1H-pyrazol-5-yl)-4-chlorophenoxy]-3-cyano-N-1,3-thiazol-4-ylbenzenesulfonamide, Example 809 (500 mg, 0.000797 mol) in methanol (4 mL) and dichloromethane (4 mL) was added triethylamine (161 mg, 0.00159 mol) and the reaction cooled to 0° C. in an ice/water bath. To the suspension was added sodium triacetoxyborohydride (422 mg, 0.00199 mol) and the reaction was then stirred at 0° C. for 10 minutes. Acetaldehyde (105 mg, 0.00239 mol) was added dropwise and the reaction stirred at 0° C. for 1.5 hours. The solvent was removed in vacuo to give an orange oil which was partitioned between dichloromethane (25 mL) and water (25 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (2×20 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (20 mL) and filtered through a phase separator. The solvent was removed in vacuo to give a pink solid which was triturated in hot ethyl acetate (10.0 mL), allowed to cool to room temperature and then filtered to give the title compound as a white solid, (431 mg).

後処理

  1. stirringthe reaction stirred at 0° C. for 1.5 hours
  2. customThe solvent was removed in vacuo
  3. customto give an orange oil which
  4. customwas partitioned between dichloromethane (25 mL) and water (25 mL)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with dichloromethane (2×20 mL)
  7. washThe combined organic layers were washed with saturated aqueous sodium chloride solution (20 mL)
  8. filtrationfiltered through a phase separator
  9. customThe solvent was removed in vacuo
  10. customto give a pink solid which
  11. customwas triturated in hot ethyl acetate (10.0 mL)
  12. temperatureto cool to room temperature
  13. filtrationfiltered

出典と根拠

ORDレコード
ord-891cc68e08ef41a3864bcebab735f688
出典データセット
uspto-grants-2014_12
特許番号
US08907101B2

反応ノート

読み込み中…