Cesium carbonate → HCID 178489070, compound

HRID 2174098Notes

Reaction equation

HRID 2174098 reaction equation
[C:1]([C:3]1[CH:39]=[CH:38][C:6]2[NH:7][C:8]([C:10]([C:19]3[C:27]([O:28][CH3:29])=[CH:26][C:25]([CH3:30])=[C:24]4[C:20]=3[CH:21]=[CH:22][N:23]4C(OC(C)(C)C)=O)([NH:15][CH2:16][CH2:17][OH:18])[C:11]([F:14])([F:13])[F:12])=[N:9][C:5]=2[CH:4]=1)#[N:2].C([O-])([O-])=O.[Cs+].[Cs+]>CO>[F:13][C:11]([F:12])([F:14])[C:10]([C:8]1[NH:7][C:6]2[CH:38]=[CH:39][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[N:9]=1)([NH:15][CH2:16][CH2:17][OH:18])[C:19]1[C:27]([O:28][CH3:29])=[CH:26][C:25]([CH3:30])=[C:24]2[C:20]=1[CH:21]=[CH:22][NH:23]2

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 178488597HCID 178488597, compound

Product 1

HCID 178489070HCID 178489070, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (±)-tert-butyl 4-(1-(5-cyano-1H-benzo[d]imidazol-2-yl)-2,2,2-trifluoro-1-((2-hydroxyethyl)amino)ethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (20 mg, 0.037 mmol) in MeOH (0.368 mL) at room temperature under nitrogen, Cs2CO3 (59.9 mg, 0.184 mmol) was added and the reaction was stirred at 60° C. After 90 minutes the reaction was cooled, quenched with NH4Cl, extracted with EtOAc, dried with MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-100% EtOAc in heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.48-12.70 (m, 1H) 10.99 (br. s., 1H) 8.27 (m) 7.89 (m) 7.81 (m) 7.56 (dd, J=8.34, 1.52 Hz, 1H) 7.48 (m) 7.06-7.21 (m, 1H) 6.81 (s, 1H) 6.01 (br. s., 1H) 4.48 (t, J=5.24 Hz, 1H) 3.34-3.54 (m, 5H) 2.56-2.72 (m, 1H) 2.46 (s, 3H) 2.01 (br. s., 1H). HRMS calcd. for C22H20F3N5O2 (M+H)+ 444.1647. found 444.1656.

Workup

  1. temperatureAfter 90 minutes the reaction was cooled
  2. customquenched with NH4Cl
  3. extractionextracted with EtOAc
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash chromatography (0-100% EtOAc in heptanes)

Sources & evidence

ORD record
ord-18be093986ec44b0806eb84aeaf48d76
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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