Ethanol → HCID 57424845, compound

HRID 656581Notes

Reaction equation

HRID 656581 reaction equation
C([NH:4][C:5]([NH2:7])=[NH:6])(=O)C.N1CCCC1.CCO.[Br:16][C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[C@@H:24]1[NH:29][C:28](=[O:30])/[C:27](=[C:31](/O)\[CH3:32])/[C:26](=O)[CH2:25]1>CCOC(C)=O>[NH2:7][C:5]1[N:4]=[C:31]([CH3:32])[C:27]2[C:28](=[O:30])[NH:29][C@@H:24]([C:18]3[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:17]=3[Br:16])[CH2:25][C:26]=2[N:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 31268PyrrolidineHCID 178467284HCID 178467284, compoundHCID 178475102HCID 178475102, compound

Product 1

HCID 57424845HCID 57424845, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

A microwave vial charged with acetylguanidine (800 mg, 7.9 mmol) was added pyrrolidine (3.25 mL, 39 mmol), 5 mL of EtOH and 31G (1.3 g, 3.9 mmol). The mixture was heated in a microwave at 160° C. for 10 min. The reaction mixture was diluted with EtOAc (50 mL) and washed with 1M NaHSO4 (40 mL×2), brine, dried over Na2SO4, concentrated in vacuo. The resulting solid was purified by column chromatography (2-5% MeOH in DCM gradient) to give the product 31H as a light yellow crystalline solid (989 mg, 72%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.61 (s, 3H) 2.83 (dd, J=16.29, 5.94 Hz, 1H) 3.22 (dd, J=16.42, 6.06 Hz, 1H) 4.84-5.06 (m, 1H) 7.11 (br. s., 2H) 7.19-7.40 (m, 2H) 7.61 (dd, J=8.59, 2.53 Hz, 1H) 7.98 (d, J=3.28 Hz, 4H). ESI-MS: m/z 351.0 (MH+).

Workup

  1. washwashed with 1M NaHSO4 (40 mL×2), brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting solid was purified by column chromatography (2-5% MeOH in DCM gradient)

Sources & evidence

ORD record
ord-522a4104488a4489b1421a4fc195e6e1
Source dataset
uspto-grants-2011_12
Patent number
US08071766B2

Reaction notes

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