HCID 59239149, compound → HCID 66679192, compound
Reaction equation
C(NC(=O)NC1C=CC(C2N=C(N3CCOC[C@@H]3C)C3CCN(C(OC(C)(C)C)=O)CC=3N=2)=CC=1)C.Cl[C:38]1[N:39]=[C:40]([N:52]2[CH2:57][CH2:56][O:55][CH2:54][C@@H:53]2[CH3:58])[C:41]2[CH2:46][N:45]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:44][C:42]=2[N:43]=1.[OH:59][CH2:60][C:61]1[CH:66]=[CH:65][C:64]([NH:67][C:68]([NH:70][C:71]2[CH:76]=[CH:75][C:74](B3OC(C)(C)C(C)(C)O3)=[CH:73][CH:72]=2)=[O:69])=[CH:63][CH:62]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:59][CH2:60][C:61]1[CH:62]=[CH:63][C:64]([NH:67][C:68](=[O:69])[NH:70][C:71]2[CH:72]=[CH:73][C:74]([C:38]3[N:39]=[C:40]([N:52]4[CH2:57][CH2:56][O:55][CH2:54][C@@H:53]4[CH3:58])[C:41]4[CH2:46][N:45]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:44][C:42]=4[N:43]=3)=[CH:75][CH:76]=2)=[CH:65][CH:66]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Method as described for intermediate 5 using (S)-ethyl 2-chloro-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate (intermediate 11) and 1-(4-(hydroxymethyl)phenyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea as starting materials, and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) as catalyst. The reaction mixture was filtered through a celite 545 pre-packed cartridge (2.5 g), washed with MeOH and solvent removed in vacuo. The residue was purified first by prep HPLC (low pH) yielding the title compound (34 mg, 0.06 mmol, 41%).
Workup
- filtrationThe reaction mixture was filtered through a celite 545 pre-packed cartridge (2.5 g)
- washwashed with MeOH and solvent
- customremoved in vacuo
- customThe residue was purified first by prep HPLC (low pH)
Sources & evidence
- ORD record
- ord-5dfc0cccfdf04967a03babebb1d7973c
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785457B2
Reaction notes
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