N,N-Dimethyl-1,3-propanediamine → N-(3-(Dimethylamino)propyl)-4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenyl-amino)thieno[2,3-d]pyrimidine-6-carboxamide mono formate salt

HRID 450550노트

반응식

HRID 450550 반응식
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]2[C:34]3[CH:41]=[C:40]([C:42]([OH:44])=[O:43])[S:39][C:35]=3[N:36]=[CH:37][N:38]=2)=[C:28]([O:45][CH:46]2[CH2:51][CH2:50][O:49][CH2:48][CH2:47]2)[CH:27]=1.CCN(C(C)C)C(C)C.[CH3:61][N:62]([CH3:67])[CH2:63][CH2:64][CH2:65][NH2:66]>CN(C=O)C>[CH:42]([OH:44])=[O:43].[CH3:61][N:62]([CH3:67])[CH2:63][CH2:64][CH2:65][NH:66][C:42]([C:40]1[S:39][C:35]2[N:36]=[CH:37][N:38]=[C:33]([NH:32][C:29]3[CH:30]=[CH:31][C:26]([F:25])=[CH:27][C:28]=3[O:45][CH:46]3[CH2:47][CH2:48][O:49][CH2:50][CH2:51]3)[C:34]=2[CH:41]=1)=[O:43]

참가 물질

6

반응물 4

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 461820834-(4-Fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)thieno[2,3-d]pyrimidine-6-carboxylic acid

생성물 1

HCID 46182172N-(3-(Dimethylamino)propyl)-4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenyl-amino)thieno[2,3-d]pyrimidine-6-carboxamide mono formate salt수율 20.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

HATU (0.054 g, 0.14 mmol) was added into a solution of 4-(4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)phenylamino)thieno[2,3-d]pyrimidine-6-carboxylic acid (0.050 g, 0.13 mmol) and Hünig's base (22 μL, 0.13 mmol) in anhydrous DMF (1.0 mL) at 0° C. After 0.5 hours, 3-dimethylamino-1-propylamine (71 μL, 0.64 mmol) was added and the solution allowed to warm to ambient temperature over night. The reaction was concentrated in vacuo and the residue redissolved in dimethyl sulfoxide. The sample was purified by reverse phase preparative HPLC to yield off-white solid (0.007 g, 11%) as the mono-formate salt.

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue redissolved in dimethyl sulfoxide
  3. customThe sample was purified by reverse phase preparative HPLC

출처 및 근거

ORD 기록
ord-739df0d75a034095bc2487acb16af76c
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486953B2

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