Water → N-1,2-Benzisoxazol-3-yl-4-(3-pyrrolidin-1-yl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide

HRID 2263006ノート

反応式

HRID 2263006 の反応式
Cl[C:2]1[S:6][N:5]=[C:4]([N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[N:3]=1.FC(F)(F)C(O)=O.[O:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:21]([NH:28][C:29]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[O:30])=[N:20]1.C(N(CC)CC)C.O>CN(C)C=O>[O:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:21]([NH:28][C:29]([N:31]2[CH2:36][CH2:35][N:34]([C:2]3[S:6][N:5]=[C:4]([N:7]4[CH2:11][CH2:10][CH2:9][CH2:8]4)[N:3]=3)[CH2:33][CH2:32]2)=[O:30])=[N:20]1

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 652686795-Chloro-3-(pyrrolidin-1-yl)-1,2,4-thiadiazoleHCID 68778018N-1,2-Benzisoxazol-3-ylpiperazine-1-carboxamide trifluoroacetate

生成物 1

HCID 68778591N-1,2-Benzisoxazol-3-yl-4-(3-pyrrolidin-1-yl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 5-chloro-3-pyrrolidin-1-yl-1,2,4-thiadiazole (158 mg, 0.833 mmol) and N-1,2-benzisoxazol-3-ylpiperazine-1-carboxamide trifluoroacetate (300 mg, 0.833 mmol) in N,N-dimethylformamide (3 ml) was added triethylamine (0.581 ml, 4.17 mmol) at room temperature, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured to water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the desired product as a solid. The resulting solid was recrystallized from a mixed solvent of hexane and ethyl acetate to give 28.5 mg (8.58%) of the desired product.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-130fbb7ddafe4e868e57e5f62ff1c8df
出典データセット
uspto-grants-2010_12
特許番号
US07851473B2

反応ノート

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