Ammonia → HCID 22252177, compound

HRID 1637887Notes

Reaction equation

HRID 1637887 reaction equation
[O:1]=[C:2]([N:15]1[CH2:27][CH2:26][C:25]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][C:17]=2[CH:16]1[C:28]1[CH:33]=[CH:32][C:31]2[O:34][CH2:35][O:36][C:30]=2[CH:29]=1)/[CH:3]=[CH:4]/[C:5]1[CH:14]=[CH:13][C:8]([C:9](OC)=[O:10])=[CH:7][CH:6]=1.[NH3:37]>CO>[O:1]=[C:2]([N:15]1[CH2:27][CH2:26][C:25]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][C:17]=2[CH:16]1[C:28]1[CH:33]=[CH:32][C:31]2[O:34][CH2:35][O:36][C:30]=2[CH:29]=1)/[CH:3]=[CH:4]/[C:5]1[CH:14]=[CH:13][C:8]([C:9]([NH2:37])=[O:10])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 131721749HCID 131721749, compound

Product 1

HCID 22252177HCID 22252177, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

Into a solution of Example 28 (0.2 g, 0.4 mmol) in 50 mL of MeOH was bubbled ammonia and the resulting mixture was stirred at 35° C. for two days. The mixture was concentrated in vacuo to give a residue which was washed with 2×30 mL of water. Extraction, drying over MgSO4 and concentration in vacuo gave a residue that was purified via radial chromatography using DCM:MeOH (90:10) as eluting solvent and via preparative chromatography (20×20- cm plate, 0.5 mm, SiO2) using the same eluant. The title compound (0.025 g, 13%) was isolated as white crystals after recrystallization from MeOH:H2O. MP: 183° C.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto give a residue which
  3. washwas washed with 2×30 mL of water
  4. extractionExtraction
  5. dry with materialdrying over MgSO4 and concentration in vacuo
  6. customgave a residue that
  7. customwas purified via radial chromatography
  8. washas eluting solvent

Sources & evidence

ORD record
ord-135b843f79f847f487174997ba18253c
Source dataset
uspto-grants-2000_03
Patent number
US06043252

Reaction notes

Loading…