Triethylamine → 1-(Benzo[1,2,3]thiadiazole-5-carbonyl)-piperidin-4-one

HRID 1293538

반응식

HRID 1293538 반응식
C1N=CN(C(N2C=NC=C2)=O)C=1.[S:13]1[C:17]2[CH:18]=[CH:19][C:20]([C:22]([OH:24])=O)=[CH:21][C:16]=2[N:15]=[N:14]1.Cl.[NH:26]1[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[S:13]1[C:17]2[CH:18]=[CH:19][C:20]([C:22]([N:26]3[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]3)=[O:24])=[CH:21][C:16]=2[N:15]=[N:14]1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 27354581,2,3-Benzothiadiazole-5-carboxylic acidHCID 30848514-Piperidone hydrochloride

생성물 1

HCID 223974651-(Benzo[1,2,3]thiadiazole-5-carbonyl)-piperidin-4-one수율 29.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

CDI (4.5 g) added to a solution of the benzo[1,2,3]thiadiazole-5-carboxylic acid (5 g) stirring in THF (100 ml) at RT. After 1 hour 4-piperidone hydrochloride (3.7 g) and triethylamine (4.3 ml) were added and the mixture stirred overnight. The resulting mixture was diluted with ethyl acetate, washed with 2M HCl (100 ml), saturated NaHCO3 solution (200 ml) and then with saturated brine (200 ml). The organic layer was dried (MgSO4) and evaporated to leave a residue which was purified by column chromatography (silica, eluting with mixtures of ethyl acetate in dichloromethane) to give the product as a yellow oil (2.1 g; MS: APCI+(M+H)262).

후처리

  1. washwashed with 2M HCl (100 ml), saturated NaHCO3 solution (200 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated
  4. customto leave a residue which
  5. customwas purified by column chromatography (silica, eluting with mixtures of ethyl acetate in dichloromethane)

출처 및 근거

ORD 기록
ord-5cbbd9b1003a49f3a3a7bfa41754bdf2
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238811B2

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