Triethylamine → 3-Chloropropane-1-sulfonic acid [2-(4-cyclopropyl-piperazin-1-yl)benzooxazol-5-ylmethyl]amide

HRID 1619275ノート

反応式

HRID 1619275 の反応式
[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[O:11][C:12]4[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.C[CH2:20][N:21](CC)CC.[Cl:26][CH2:27][CH2:28][CH2:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl>[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[O:11][C:12]4[CH:18]=[CH:17][C:16]([CH2:20][NH:21][S:30]([CH2:29][CH2:28][CH2:27][Cl:26])(=[O:32])=[O:31])=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 474536642-(4-Cyclopropylpiperazin-1-yl)benzooxazole

生成物 1

HCID 595887923-Chloropropane-1-sulfonic acid [2-(4-cyclopropyl-piperazin-1-yl)benzooxazol-5-ylmethyl]amide収率 42%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 5-aminomethyl-[2-(4-cyclopropylpiperazin-1-yl)benzooxazole (500 mg, 1.84 mmol) in CH2Cl2 (15 mL) was added Et3N (929 mg, 9.2 mmol). The mixture was stirred at 0° C. for 5 min and then 3-chloropropane-1-sulfonyl chloride (326 mg, 1.84 mmol) was added dropwise. The mixture was stirred at 0° C. for 1 h and brought gradually to rt. Then the mixture was stirred for another 1 h. The volatiles were removed and the residue was extracted with CH2Cl2. The resulting residue was purified by column chromatography on silica gel (elute: 5% CH2Cl2 in methanol) to give 3-chloropropane-1-sulfonic acid [2-(4-cyclopropyl-piperazin-1-yl)benzooxazol-5-ylmethyl]amide (315 mg, 42%).

後処理

  1. stirringThe mixture was stirred at 0° C. for 1 h
  2. custombrought gradually to rt
  3. stirringThen the mixture was stirred for another 1 h
  4. customThe volatiles were removed
  5. extractionthe residue was extracted with CH2Cl2
  6. customThe resulting residue was purified by column chromatography on silica gel (elute: 5% CH2Cl2 in methanol)

出典と根拠

ORDレコード
ord-ec2f356bdb274055bba56f84aacd1ecf
出典データセット
uspto-grants-2014_07
特許番号
US08772285B2

反応ノート

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