1-Ethyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea → HCID 66678978, compound

HRID 1626688Notes

Reaction equation

HRID 1626688 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[C:5]2[CH2:10][N:9]([CH3:11])[CH2:8][C:6]=2[N:7]=1.[CH2:19]([NH:21][C:22]([NH:24][C:25]1[CH:30]=[CH:29][C:28](B2OC(C)(C)C(C)(C)O2)=[C:27]([F:40])[CH:26]=1)=[O:23])[CH3:20]>>[CH2:19]([NH:21][C:22]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[N:3]=[C:4]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]3[CH3:18])[C:5]3[CH2:10][N:9]([CH3:11])[CH2:8][C:6]=3[N:7]=2)=[C:27]([F:40])[CH:26]=1)=[O:23])[CH3:20]

Participants

3

Reactant 2

HCID 666787871-Ethyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea2×HCID 86663154(S)-4-(2-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine2×

Product 1

HCID 66678978HCID 66678978, compoundYield 4%

Procedure

Method as described for example 147 using (S)-4-(2-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine (intermediate 12) and 1-ethyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (intermediate 28) as starting materials. The crude reaction mixture was partitioned between EtOAc (25 ml) and water (25 ml). The organic layer was recovered, passed through a hydrophobic fit and the solvent removed in vacuo. Residue was then purified by prep. HPLC at low pH to afford a yellow solid (8.4 mg, 0.02 mmol, 4%).

Workup

  1. customThe crude reaction mixture
  2. customwas partitioned between EtOAc (25 ml) and water (25 ml)
  3. customThe organic layer was recovered
  4. customthe solvent removed in vacuo
  5. customResidue was then purified by prep

Sources & evidence

ORD record
ord-d608b7b06a1c4f0099d966f0482e1c77
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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