HCID 66687782, compound → HCID 66679196, compound

HRID 1626671Notes

Reaction equation

HRID 1626671 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][C@@H:17]2[CH3:22])[C:5]2[CH2:10][N:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:8][C:6]=2[N:7]=1.[F:23][C:24]1[CH:25]=[C:26]([CH:28]=[C:29]([F:40])[C:30]=1B1OC(C)(C)C(C)(C)O1)[NH2:27]>>[CH2:8]([NH:9][C:11](=[O:12])[NH:27][C:26]1[CH:28]=[C:29]([F:40])[C:30]([C:2]2[N:3]=[C:4]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][C@@H:17]3[CH3:22])[C:5]3[CH2:10][N:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:8][C:6]=3[N:7]=2)=[C:24]([F:23])[CH:25]=1)[CH3:6]

Participants

3

Reactant 2

HCID 66687782HCID 66687782, compoundHCID 86663155HCID 86663155, compound2×

Product 1

HCID 66679196HCID 66679196, compoundYield 14%

Conditions

Temperature
130 °C

Procedure

Method as described for example 47 using (S)-ethyl 2-chloro-4-(3-methylmorpholino)-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate (intermediate 11) and 3,5-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline as starting materials. Reaction mixture heated in by microwave at 130° C. for 1 h. The mixture was filtered through a celite 545 pre-packed cartridge (2.5 g), washed with MeOH and the solvent removed in vacuo. The residue was purified by prep. HPLC at high pH, yielding the title compound (55 mg, 0.13 mmol, 14%).

Workup

  1. customReaction mixture
  2. filtrationThe mixture was filtered through a celite 545 pre-packed cartridge (2.5 g)
  3. washwashed with MeOH
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by prep

Sources & evidence

ORD record
ord-2cefe935576e4007a7ed9d60ff3a5223
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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