HCID 59239149, compound → (S)-2-(3-(4-(6-(ethoxycarbonyl)-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)ureido)acetic acid

HRID 1626629Notes

Reaction equation

HRID 1626629 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.CC1(C)C(C)(C)OB([C:67]2[CH:72]=[CH:71][C:70]([NH:73][C:74](=[O:80])[NH:75][CH2:76][C:77]([OH:79])=[O:78])=[CH:69][CH:68]=2)O1>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]>[CH2:50]([O:49][C:47]([N:45]1[CH2:46][C:41]2[C:40]([N:52]3[CH2:57][CH2:56][O:55][CH2:54][C@@H:53]3[CH3:58])=[N:39][C:38]([C:67]3[CH:68]=[CH:69][C:70]([NH:73][C:74](=[O:80])[NH:75][CH2:76][C:77]([OH:79])=[O:78])=[CH:71][CH:72]=3)=[N:43][C:42]=2[CH2:44]1)=[O:48])[CH3:51]

Participants

5

Reactant 3

HCID 59239149HCID 59239149, compoundHCID 666877302-(3-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureido)acetic acidHCID 86663155HCID 86663155, compound2×

Product 1

HCID 66679216(S)-2-(3-(4-(6-(ethoxycarbonyl)-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)ureido)acetic acid

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 2-(3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureido)acetic acid 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 (low pH) yielding (6.5 mg, 0.01 mmol, 9%).

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 (low pH)
  5. customyielding (6.5 mg, 0.01 mmol, 9%)

Sources & evidence

ORD record
ord-afa30fac6e1744c395800677c053dbda
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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