Hydrochloric Acid → 4-fluoro-N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-benzamide

HRID 51844

반응식

HRID 51844 반응식
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C.[CH3:44][O:45][C:46]1[C:51]2[N:52]=[C:53]([NH2:55])[S:54][C:50]=2[C:49]([N:56]([CH2:58][CH2:59][O:60][CH3:61])[CH3:57])=[CH:48][CH:47]=1.Cl>C1COCC1.O1CCOCC1.CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:55][C:53]2[S:54][C:50]3[C:49]([N:56]([CH2:58][CH2:59][O:60][CH3:61])[CH3:57])=[CH:48][CH:47]=[C:46]([O:45][CH3:44])[C:51]=3[N:52]=2)=[O:8])=[CH:9][CH:10]=1

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 99734-Fluorobenzoic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 220157444-methoxy-N7-(2-methoxy-ethyl)-N7-methyl-benzothiazole-2,7-diamine

생성물 1

HCID 101265534-fluoro-N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-benzamide수율 25.2%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 312751,4-Dioxane용매

실험 절차

To a stirred solution of 79 mg (0.56 mmol) 4-fluoro-benzoic acid in 10 ml THF were added 235 mg (0.62 mmol) HATU and 0.11 ml (0.62 mmol) N-ethyldiisopropylamine and stirring continued at room temperature for 1 h. A solution of 150 mg (0.56 mmol) 4-methoxy-N7-(2-methoxy-ethyl)-N7-methyl-benzothiazole-2,7-diamine in 5 ml dioxane and 1 ml DMF was then added and stirring continued at room temperature for 16 h. The reaction mixture was then poured into 100 ml 1 M hydrochloric acid and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1/4-1/1 ethyl acetate/hexane) followed by trituration in hexane afforded 55 mg (25%) 4-fluoro-N-{4-methoxy-7-[(2-methoxy-ethyl)-methyl-amino]-benzothiazol-2-yl}-benzamide as an off-white crystalline solid. ES-MS m/e (%): 390 (M+H+, 100).

후처리

  1. stirringstirring
  2. waitcontinued at room temperature for 16 h
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-6413f97c041a4449bed82926c1d1bab4
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713499B2

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