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 450550ノート

反応式

HRID 450550 の反応式
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]

参加物

6

反応物 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

生成物 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 salt収率 20.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-739df0d75a034095bc2487acb16af76c
出典データセット
uspto-grants-2013_07
特許番号
US08486953B2

反応ノート

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