Cesium carbonate → HCID 59351177, compound

HRID 887444Notes

Reaction equation

HRID 887444 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[O:11].F[C:20]1[C:25]([C:26]2([F:32])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[N:24][CH:23]=[CH:22][N:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:20]2[C:25]([C:26]3([F:32])[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)=[N:24][CH:23]=[CH:22][N:21]=2)=[CH:14][CH:13]=1)=[O:11]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 59326874(1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanoneHCID 593511352-Fluoro-3-(4-fluorotetrahydro-2H-pyran-4-YL)pyrazine

Product 1

HCID 59351177HCID 59351177, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of (1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone (0.543 g, 2.278 mmol), 2-fluoro-3-(4-fluorotetrahydro-2H-pyran-4-yl)pyrazine (0.304 g, 1.519 mmol), cesium carbonate (0.990 g, 3.04 mmol), and N-Methyl-2-pyrrolidinone (3.04 mL) in a sealed tube was heated to 100° C. overnight. Aqueous work up with DCM and washing with alternating water and brine washes. The organic layer was rotovapped and loaded onto a Biotage samplet. Purification by Biotage (0-100% EtOAc/hexane, slow gradient, over 12 CV). The product containing fractions were concentrated by rotovap. The residue was further purified by trituration with EtOH at room temperature overnight to produce product. MS (ESI, pos. ion) m/z: 419.1 (M+1). IC50 (uM) +++++.

Workup

  1. washAqueous work up with DCM and washing with alternating water and brine washes
  2. customPurification by Biotage (0-100% EtOAc/hexane, slow gradient, over 12 CV)
  3. additionThe product containing fractions
  4. concentrationwere concentrated by rotovap
  5. customThe residue was further purified by trituration with EtOH at room temperature overnight
  6. customto produce product

Sources & evidence

ORD record
ord-1de73b9897d248aab626b330e867ad51
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

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