Formic Acid → 4-t-butyl-N-[2-(4-formylpiperazinyl)-6-(3-hydroxypropyloxy)-5-(2-methoxyphenoxy)-4-pyrimidinyl]benzenesulfonamide

HRID 1418346ノート

反応式

HRID 1418346 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:19]([O:30][CH2:31][CH2:32][CH2:33][OH:34])[N:18]=[C:17]([N:35]3[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.[CH:63](O)=[O:64].Cl>CN(C)C=O.C(Cl)Cl.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:19]([O:30][CH2:31][CH2:32][CH2:33][OH:34])[N:18]=[C:17]([N:35]3[CH2:36][CH2:37][N:38]([CH:63]=[O:64])[CH2:39][CH2:40]3)[N:16]=2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

8

反応物 5

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 700223014-t-Butyl-N-[6-(3-hydroxypropyloxy)-5-(2-methoxyphenoxy)-2-piperazinyl-4-pyrimidinyl]-benzenesulfonamide

生成物 1

HCID 867538784-t-butyl-N-[2-(4-formylpiperazinyl)-6-(3-hydroxypropyloxy)-5-(2-methoxyphenoxy)-4-pyrimidinyl]benzenesulfonamide収率 23.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 22350042dichloromethane N,N-dimethylformamide溶媒

実験手順

4-t-Butyl-N-[6-(3-hydroxypropyloxy)-5-(2-methoxyphenoxy)-2-piperazinyl-4-pyrimidinyl]-benzenesulfonamide (80 mg; 0.14 mmol), WSC·HCl (61.6 mg; 0.28 mmol), N-hydroxybenzotriazole (75.6 mg; 0.56 mmol), and formic acid (6.5 mg; 0.15 mmol) were dissolved in dimethylformamide-methylene chloride (1:1, 1 ml). The mixture was stirred overnight at room temperature. The reaction mixture was poured into water, made acidic with hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and evaporated. The residue was purified by silica gel column chromatography (chloroform:methanol=15:1), to thereby obtain 20 mg (yield: 23.8%) of the title compound as a pale yellow oil.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol=15:1)

出典と根拠

ORDレコード
ord-c4e0b269fc19486bb7956b2a5b74ea19
出典データセット
uspto-grants-1999_03
特許番号
US05883092

反応ノート

読み込み中…