4-Fluorobenzoic Acid → N-(7-dimethylamino-4-methoxy-benzothiazol-2-yl)-4-fluoro-benzamide

HRID 51869

反応式

HRID 51869 の反応式
[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]([CH3:58])[CH3:57])=[CH:48][CH:47]=1>C1COCC1>[CH3:57][N:56]([CH3:58])[C:49]1[C:50]2[S:54][C:53]([NH:55][C:6](=[O:8])[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)=[N:52][C:51]=2[C:46]([O:45][CH3:44])=[CH:47][CH:48]=1

参加物

6

反応物 4

HCID 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 227370024-methoxy-N7,N7-dimethyl-benzothiazole-2,7-diamine

生成物 1

HCID 10125964N-(7-dimethylamino-4-methoxy-benzothiazol-2-yl)-4-fluoro-benzamide収率 84.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 41 mg (0.29 mmol) 4-fluoro-benzoic acid in 1 ml THF were added 128 mg (0.34 mmol) HATU and 0.10 ml (0.56 mmol) N-ethyldiisopropylamine and stirring continued at room temperature for 2.5 h. 50 mg (0.22 mmol) 4-methoxy-N7,N7-dimethyl-benzothiazole-2,7-diamine was then added and stirring continued at room temperature for 16 h. The reaction mixture was then concentrated in vactio. Flash chromatography (ethyl acetate/hexane) afforded 64 mg (83%) N-(7-dimethylamino-4-methoxy-benzothiazol-2-yl)-4-fluoro-benzamide as a white crystalline solid. ES-MS m/e (%): 346 (M+H +, 100).

後処理

  1. stirringstirring
  2. waitcontinued at room temperature for 16 h
  3. concentrationThe reaction mixture was then concentrated in vactio

出典と根拠

ORDレコード
ord-53a2b0ee2029483f8559cf5ac8085b3f
出典データセット
uspto-grants-2004_03
特許番号
US06713499B2

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