Triethylamine → (4-Difluoromethoxy-phenyl)-{4-[1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-methanone

HRID 1958381

반응식

HRID 1958381 반응식
[F:1][CH:2]([F:13])[O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[F:39][C:40]1[CH:45]=[C:44]([S:46]([CH3:49])(=[O:48])=[O:47])[CH:43]=[CH:42][C:41]=1[N:50]1[C:54]2=[N:55][CH:56]=[N:57][C:58]([O:59][CH:60]3[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]3)=[C:53]2[CH:52]=[N:51]1.C(N(CC)CC)C>CN(C=O)C>[F:13][CH:2]([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:63]2[CH2:64][CH2:65][CH:60]([O:59][C:58]3[N:57]=[CH:56][N:55]=[C:54]4[N:50]([C:41]5[CH:42]=[CH:43][C:44]([S:46]([CH3:49])(=[O:48])=[O:47])=[CH:45][C:40]=5[F:39])[N:51]=[CH:52][C:53]=34)[CH2:61][CH2:62]2)=[O:10])=[CH:11][CH:12]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 7373604-(Difluoromethoxy)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 218977401-(2-Fluoro-4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine hydrochloride

생성물 1

HCID 21897847(4-Difluoromethoxy-phenyl)-{4-[1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-methanone수율 32%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-Difluoromethoxy-benzoic acid (527 mg, 2.8 mmol) and HATU (1.06 g, 2.8 mmol) were stirred together in DMF at room temperature for 30 min. 1-(2-Fluoro-4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine hydrochloride (800 mg, 1.87 mmol) and triethylamine (785 μL, 5.61 mmol) were added next. The resulting mixture was allowed to stir for 24 hours. Progress of the reaction was monitored by TLC and LCMS. Removal of organic solvents in vacuo and purification by HPLC afforded Compound A193 as a beige solid (127 mg, 32%). Exact mass calculated for C25H22F2N5O5S 561.53, found 562.2 (MH+)

후처리

  1. customRemoval of organic solvents
  2. customin vacuo and purification by HPLC

출처 및 근거

ORD 기록
ord-fee6d62aa1f346da93b89b847078a011
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410119B2

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