Ethyl Acetate → HCID 86345948, compound

HRID 1772742Notes

Reaction equation

HRID 1772742 reaction equation
Cl[C:2]1[C:3]2[N:4]([CH:27]=[C:28]([CH2:30][OH:31])[N:29]=2)[C:5]([C:8]2[CH:9]=[CH:10][C:11]([N:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)=[N:12][CH:13]=2)=[CH:6][N:7]=1.[NH:32]1[CH2:37][CH2:36][NH:35][CH2:34][C:33]1=[O:38].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C>[OH:31][CH2:30][C:28]1[N:29]=[C:3]2[C:2]([N:35]3[CH2:36][CH2:37][NH:32][C:33](=[O:38])[CH2:34]3)=[N:7][CH:6]=[C:5]([C:8]3[CH:9]=[CH:10][C:11]([N:14]4[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]4)=[N:12][CH:13]=3)[N:4]2[CH:27]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 231360Piperazin-2-oneHCID 117733767HCID 117733767, compound

Product 1

HCID 86345948HCID 86345948, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of compound 87c (90.0 mg, 0.202 mmol), piperazin-2-one (40.5 mg, 0.405 mmol) and K2CO3 (55.9 mg, 0.405 mmol) in 2.5 mL of DMF was stirred at 130° C. for 6 h under an Argon atmosphere. After cooling to rt, the mixture was treated with 30 mL of EtOAc and washed with saturated NH4Cl (20 mL), water (20 mL), brine (10 mL) and then dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography on silica gel (0-7 MeOH/DCM) to give compound 88a as an off white solid. 1H-NMR (CDCl3, 400 MHz): δ 8.34 (d, J=2.4 Hz, 1H), 7.67 (dd, J=8.8, 2.4 Hz, 1H), 7.54 (s, 1H), 7.30 (s, 1H), 6.76 (d, J=8.8 Hz, 1H), 6.23 (br. s., 1H), 4.89 (s, 2H), 4.80 (d, J=5.4 Hz, 2H), 4.55 (t, J=5.3 Hz, 2H), 3.55-3.69 (m, 10H), 1.50 (s, 9H). Mass spectrum (LCMS, ESI pos.): Calcd. for C25H32N8O4, 509.2 (M+H). found 509.2.

Workup

  1. temperatureAfter cooling to rt
  2. washwashed with saturated NH4Cl (20 mL), water (20 mL), brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by flash column chromatography on silica gel (0-7 MeOH/DCM)

Sources & evidence

ORD record
ord-bf8d44de34fd44ff9dc53845b28109c6
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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