Triethylamine → 6-chloro-4-methyl-N-(3-quinuclidinyl)-3,4-dihydro-2H-1,4-benzothiazine-8-carboxamide

HRID 2081555노트

반응식

HRID 2081555 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([OH:15])=O)[C:5]2[S:10][CH2:9][CH2:8][N:7]([CH3:11])[C:6]=2[CH:12]=1.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[NH2:30][CH:31]1[CH:36]2[CH2:37][CH2:38][N:33]([CH2:34][CH2:35]2)[CH2:32]1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([NH:30][CH:31]2[CH:36]3[CH2:37][CH2:38][N:33]([CH2:34][CH2:35]3)[CH2:32]2)=[O:15])[C:5]2[S:10][CH2:9][CH2:8][N:7]([CH3:11])[C:6]=2[CH:12]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 1232383-AminoquinuclidineHCID 108478516-chloro-4-methyl-3,4-dihydro-2H-1,4-benzothiazine-8-carboxylic acid

생성물 1

HCID 104981616-chloro-4-methyl-N-(3-quinuclidinyl)-3,4-dihydro-2H-1,4-benzothiazine-8-carboxamide

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

To a solution of 1.8 g of 6-chloro-4-methyl-3,4-dihydro-2H-1,4-benzothiazine-8-carboxylic acid in 30 ml of ethyl acetate was added 1.05 g of triethylamine, and then added 0.891 g of pivaloyl chloride dropwise with stirring at -10° C. to -5° C. followed by stirring the mixture at the same temperature for 30 minutes. To the resultant mixture was added a solution of 1.12 g of 3-aminoquinuclidine in 15 ml of ethyl acetate at -10° to -5° C. and then stirred at room temperature for an hour. After the reaction solution was washed with water, dried over anhydrous sodium sulfate and concentrated, the crystalline residue thus obtained was recrystallized from ethyl acetate to give 6-chloro-4-methyl-N-(3-quinuclidinyl)-3,4-dihydro-2H-1,4-benzothiazine-8-carboxamide as yellow crystals. Melting point: 195°-196° C.

후처리

  1. stirringby stirring the mixture at the same temperature for 30 minutes
  2. stirringstirred at room temperature for an hour
  3. washAfter the reaction solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customthe crystalline residue thus obtained
  7. customwas recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-23bbd03679e34015a1a68ac0b8217dff
출처 데이터셋
uspto-grants-1993_02
특허 번호
US05185333

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