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Water → N-[3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methylphenyl]-3-(trifluoromethoxy)benzamide

HRID 1800507
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Reaktionsgleichung

Reaktionsgleichung von HRID 1800507
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=O.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[NH2:39][C:40]1[CH:41]=[CH:42][C:43]([CH3:62])=[C:44]([CH:61]=1)[O:45][C:46]1[N:51]=[C:50]2[S:52][C:53]([NH:55][C:56]([CH:58]3[CH2:60][CH2:59]3)=[O:57])=[N:54][C:49]2=[CH:48][CH:47]=1.O>N1C=CC=CC=1>[CH:58]1([C:56]([NH:55][C:53]2[S:52][C:50]3[C:49]([N:54]=2)=[CH:48][CH:47]=[C:46]([O:45][C:44]2[CH:61]=[C:40]([NH:39][C:7](=[O:9])[C:6]4[CH:10]=[CH:11][CH:12]=[C:4]([O:3][C:2]([F:1])([F:14])[F:13])[CH:5]=4)[CH:41]=[CH:42][C:43]=2[CH3:62])[N:51]=3)=[O:57])[CH2:59][CH2:60]1
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Komponenten

6

Edukt 4

HCID 962WaterHCID 660963-(Trifluoromethoxy)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58451281HCID 58451281, Verbindung

Produkt 1

HCID 59506998N-[3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methylphenyl]-3-(trifluoromethoxy)benzamide
Ausbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of 3-(trifluoromethoxy)benzoic acid (37.5 mg, 0.185 mmol) in pyridine (2.0 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (70 mg, 0.185 mmol), and the mixture was stirred at room temperature for 10 min. N-[5-(5-Amino-2-methylphenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (60 mg, 0.176 mmol) produced in Example C47(i) was added to the obtained solution, and the mixture was stirred at 70° C. for 20 hr. After the reaction mixture was cooled to room temperature, water (2 mL) was added, and the obtained yellow precipitate was collected by filtration, washed with water and ethyl acetate, and dried to give the title compound (48.5 mg, 52%) as a yellow powder.

Aufarbeitung

  1. additionwas added to the obtained solution
  2. stirringthe mixture was stirred at 70° C. for 20 hr
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. filtrationthe obtained yellow precipitate was collected by filtration
  5. washwashed with water and ethyl acetate
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-647e96c32eca478f89e8b9f966fbaba1
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08344135B2

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