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Triethylamine → (4-Fluorophenyl)(2-((3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)amino)-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)methanone

HRID 604908
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HRID 604908 반응식
Cl.Cl.Cl.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([NH:18][C:19]2[S:20][C:21]3[CH2:22][NH:23][CH2:24][CH2:25][C:26]=3[N:27]=2)[CH:9]=[CH:10][C:11]=1[N:12]1[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]1.[F:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1.C(N(CC)CC)C>C(Cl)Cl>[F:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([N:23]2[CH2:24][CH2:25][C:26]3[N:27]=[C:19]([NH:18][C:8]4[CH:9]=[CH:10][C:11]([N:12]5[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]5)=[C:6]([O:5][CH3:4])[CH:7]=4)[S:20][C:21]=3[CH2:22]2)=[O:34])=[CH:31][CH:30]=1
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5

반응물 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 25106280N-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-amine trihydrochloride

생성물 1

HCID 25106282(4-Fluorophenyl)(2-((3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)amino)-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)methanone

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

90 mg (0.2 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-(4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-yl)-amine trihydrochloride and 33 mg (0.2 mmol) 4-fluorobenzoyl chloride were suspended in methylene chloride (2 ml) and 101 mg (1 mmol) triethyl amine was added at room temperature. The reaction was stirred over night, diluted with methylene chloride, washed once with water, once with brine, dried over sodium sulphate, filtered and the solvent was evaporated under reduced pressure. The reaction was purified on silica gel with methylene chloride/methanol 19/1 yielding 52 mg (56%) (4-fluoro-phenyl)-{2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl}-methanone as a yellow solid. MS ISP (m/e): 464.1 (100) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm) 10.34 (s, 1H), 7.57-7.49 (m, 3H), 7.34-7.24 (m, 4H), 7.02 (d, 1H), 4.70-4.45 (br m, 2H), 4.00-3.55 (br m, 2H), 3.78 (s, 3H), 2.73 (m, 2H), 2.14 (s, 3H).

후처리

  1. washwashed once with water, once with brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure
  5. customThe reaction was purified on silica gel with methylene chloride/methanol 19/1 yielding 52 mg (56%) (4-fluoro-phenyl)-{2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl}-methanone as a yellow solid

출처 및 근거

ORD 기록
ord-86184fe0693c4340bdaefc59d563c8f9
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07910740B2

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