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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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HRID 1800507 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 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, 화합물

생성물 1

HCID 59506998N-[3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methylphenyl]-3-(trifluoromethoxy)benzamide
수율 52.1%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-647e96c32eca478f89e8b9f966fbaba1
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08344135B2

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