Potassium Carbonate → HCID 86663057, compound

HRID 2410833Notes

Reaction equation

HRID 2410833 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:23]([NH2:25])=[O:24])[C:5]2[NH:6][C:7]3[CH:8]=[C:9]([NH:15][C:16](=[O:22])[CH2:17][O:18][CH2:19][CH2:20]Cl)[CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([C:23]([NH2:25])=[O:24])[C:5]2[NH:6][C:7]3[CH:8]=[C:9]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][C:16]4=[O:22])[CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86663056HCID 86663056, compound

Product 1

HCID 86663057HCID 86663057, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromo-7-(2-(2-chloroethoxy)acetamido)-5H-pyrido[3,2-b]indole-4-carboxamide (40 mg, 0.094 mmol) and potassium carbonate (27 mg, 0.20 mmol) in acetonitrile (2.5 mL) was stirred at 100° C. for 3 hr. The solvent was removed and preparative HPLC (100×30 mm Luna C18 column, Solvent A=10% Methanol, 90% H2O, 0.1% TFA; Solvent B=90% Methanol, 10% H2O, 0.1% TFA, 10-60% B at 42 mL/min over 20 min) followed by SCX capture and release with 2 N NH3 in MeOH left 2-bromo-7-(3-oxomorpholino)-5H-pyrido[3,2-b]indole-4-carboxamide (30 mg, 0.073 mmol, 78% yield) as a yellow solid. MS (ESI) m/z 389.02 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.84 (1H, br. s.), 8.06-8.32 (1H, m), 7.89 (2H, br. s.), 7.52-7.76 (2H, m), 7.23 (1H, br. s.), 4.16-4.36 (2H, m), 3.94-4.13 (2H, m), 3.74-3.90 (2H, m).

Workup

  1. customThe solvent was removed
  2. custompreparative HPLC (100×30 mm Luna C18 column, Solvent A=10% Methanol, 90% H2O, 0.1% TFA; Solvent B=90% Methanol, 10% H2O, 0.1% TFA, 10-60% B at 42 mL/min over 20 min)

Sources & evidence

ORD record
ord-0e635e7b70f74b098a2ca889ff146620
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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