HCID 59239149, compound → HCID 66679194, compound

HRID 1626639Notes

Reaction equation

HRID 1626639 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.[CH3:59][NH:60][C:61](=[O:82])[CH2:62][NH:63][C:64]([NH:66][C:67]1[CH:72]=[CH:71][C:70](B2OC(C)(C)C(C)(C)O2)=[CH:69][CH:68]=1)=[O:65]>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]>[CH3:59][NH:60][C:61](=[O:82])[CH2:62][NH:63][C:64](=[O:65])[NH:66][C:67]1[CH:72]=[CH:71][C:70]([C:38]2[N:39]=[C:40]([N:52]3[CH2:57][CH2:56][O:55][CH2:54][C@@H:53]3[CH3:58])[C:41]3[CH2:46][N:45]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:44][C:42]=3[N:43]=2)=[CH:69][CH:68]=1

Participants

5

Reactant 3

HCID 59239149HCID 59239149, compoundHCID 66688410HCID 66688410, compoundHCID 86663155HCID 86663155, compound2×

Product 1

HCID 66679194HCID 66679194, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

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 N-methyl-2-(3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureido)acetamide as starting materials and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) as catalyst. The 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 by prep HPLC (high pH) yielding the title compound (35 mg, 0.07 mmol, 46%).

Workup

  1. filtrationThe mixture was filtered through a celite 545 pre-packed cartridge (2.5 g)
  2. washwashed with MeOH and solvent
  3. customremoved in vacuo
  4. customThe residue was purified by prep HPLC (high pH)

Sources & evidence

ORD record
ord-0c3cf18875e849ad8c98bed44ecc23f0
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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