Reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.Cl.Cl.[Cl:28][C:29]1[N:34]=[CH:33][C:32]([C:35]2[NH:39][C:38]([C@@H:40]3[CH2:44][CH2:43][CH2:42][NH:41]3)=[N:37][CH:36]=2)=[CH:31][N:30]=1.[N:45]1[CH:50]=[CH:49][CH:48]=[C:47]([CH2:51][C:52](O)=[O:53])[CH:46]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:28][C:29]1[N:34]=[CH:33][C:32]([C:35]2[NH:39][C:38]([C@@H:40]3[CH2:44][CH2:43][CH2:42][N:41]3[C:52](=[O:53])[CH2:51][C:47]3[CH:46]=[N:45][CH:50]=[CH:49][CH:48]=3)=[N:37][CH:36]=2)=[CH:31][N:30]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
HATU (0.60 g, 1.57 mmol) was added in one portion to a stirred solution of intermediate (S)-2-chloro-5-(2-(pyrrolidin-2-yl)-1H-imidazol-5-yl)pyrimidine trihydrochloride (0.46 g, 1.43 mmol, theoretical amount), 2-(pyridin-3-yl)acetic acid (0.25 g, 1.43 mmol) and DIEA (1.0 mL, 5.72 mmol) in anhydrous DMF (10 mL) at ambient temperature. The mixture was stirred at room temperature for 2 h before the DMF was removed in vacuo. The residue was taken up in CH2Cl2 and subjected to Biotage™ flash chromatography on silica gel (40M column, preequilibration with 0% B for 600 mL followed by step gradient elution with 0% B to 0% B for 150 mL followed by 0% B to 15% B for 1500 mL followed by 15% B to 25% B for 999 mL where B=MeOH and A=CH2Cl2). There was isolated the title compound (0.131 g, 25%, 2 steps) as a yellow solid.
Workup
- customwas removed in vacuo
- washfollowed by step gradient elution with 0% B to 0% B for 150 mL
Sources & evidence
- ORD record
- ord-4de6fdb303464d76a7e0a22466b09f8b
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745636B2
Linked notes
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