HCID 59239149, compound → HCID 66694087, compound

HRID 1626638Notes

Reaction equation

HRID 1626638 reaction equation
[CH2:1]([NH:3][C:4](=[O:36])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]3[CH3:35])[C:15]3C[CH2:20][N:19]([C:22]([O:24][C:25](C)(C)[CH3:26])=[O:23])[CH2:18][C:16]=3[N:17]=2)=[CH:8][CH:7]=1)[CH3:2].ClC1N=C(N2CCOC[C@@H]2C)C2CN(C(OCC)=O)CC=2N=1.CC1(C)C(C)(C)OB(C2C=CC(NC(=O)NCC[NH:78][C:79](=[O:81])[CH3:80])=CC=2)O1>Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:79]([NH:78][CH2:2][CH2:1][NH:3][C:4](=[O:36])[NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:13]=[C:14]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]3[CH3:35])[C:15]3[CH2:20][N:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][C:16]=3[N:17]=2)=[CH:10][CH:11]=1)(=[O:81])[CH3:80]

Participants

6

Reactant 3

HCID 59239149HCID 59239149, compoundHCID 66686958HCID 66686958, compoundHCID 86663155HCID 86663155, compound2×

Product 1

HCID 66694087HCID 66694087, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)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-(2-(3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureido)ethyl)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 (30 mg, 0.05 mmol, 38%).

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-6ba7b52f983b491fa81520be79d0bd4a
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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