N,N-Dimethylglycine → 2-dimethylamino-1-{4-[4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)-phenylamino]-5,8-dihydro-6H-pyrido[4',3':4,5]thieno[2,3-d]pyrimidin-7-yl}-ethanone

HRID 450575노트

반응식

HRID 450575 반응식
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:34][N:35]([CH3:40])[CH2:36][C:37](O)=[O:38].[F:41][C:42]1[CH:47]=[CH:46][C:45]([NH:48][C:49]2[C:50]3[C:57]4[CH2:58][CH2:59][NH:60][CH2:61][C:56]=4[S:55][C:51]=3[N:52]=[CH:53][N:54]=2)=[C:44]([O:62][CH:63]2[CH2:68][CH2:67][O:66][CH2:65][CH2:64]2)[CH:43]=1>CN(C=O)C.O>[CH3:34][N:35]([CH3:40])[CH2:36][C:37]([N:60]1[CH2:59][CH2:58][C:57]2[C:50]3[C:49]([NH:48][C:45]4[CH:46]=[CH:47][C:42]([F:41])=[CH:43][C:44]=4[O:62][CH:63]4[CH2:68][CH2:67][O:66][CH2:65][CH2:64]4)=[N:54][CH:53]=[N:52][C:51]=3[S:55][C:56]=2[CH2:61]1)=[O:38]

참가 물질

7

반응물 4

HCID 673N,N-DimethylglycineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 46182217[4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)-phenyl]-(5,6,7,8-tetrahydro-pyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-yl)-amine

생성물 1

HCID 461822182-dimethylamino-1-{4-[4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)-phenylamino]-5,8-dihydro-6H-pyrido[4',3':4,5]thieno[2,3-d]pyrimidin-7-yl}-ethanone수율 40.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

HATU (0.285 g, 0.75 mmol) was added into a stirred solution of Hünig's base (0.13 mL, 0.75 mmol) and N,N-dimethylglycine (0.077 g, 0.75 mmol) in DMF (1.0 mL) and the mixture stirred for 20 minutes at ambient temperature. [4-Fluoro-2-(tetrahydro-2H-pyran-4-yloxy)-phenyl]-(5,6,7,8-tetrahydro-pyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4-yl)-amine (0.10 g, 0.25 mmol) was added and the mixture stirred for 18 hours. Water (5 mL) was added and the mixture stirred for 20 minutes. The precipitated solid was collect by filtration, washed with water (10 mL), diethyl ether (10 mL), and dried under vacuum to give a colourless solid (0.049 g, 40%).

후처리

  1. stirringthe mixture stirred for 18 hours
  2. stirringthe mixture stirred for 20 minutes
  3. filtrationThe precipitated solid was collect by filtration
  4. washwashed with water (10 mL), diethyl ether (10 mL)
  5. customdried under vacuum

출처 및 근거

ORD 기록
ord-27991f20f2bd4009be2b3a54382c10df
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486953B2

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