Ammonia → HCID 11433093, compound

HRID 1455665Notes

Reaction equation

HRID 1455665 reaction equation
[CH3:1][C:2]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([CH2:24][C:25]([C:27]4[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=4)=O)[CH:21]=[CH:22][CH:23]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([S:4]([CH3:7])(=[O:6])=[O:5])[CH3:3].[NH3:37].[C:38]([O:42]C)(=O)[C:39]#[CH:40]>CO>[CH3:1][C:2]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([C:24]4[CH:40]=[CH:39][C:38](=[O:42])[NH:37][C:25]=4[C:27]4[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=4)[CH:21]=[CH:22][CH:23]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([S:4]([CH3:7])(=[O:6])=[O:5])[CH3:3]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 13536Methyl propiolateHCID 10208267HCID 10208267, compound

Product 1

HCID 11433093HCID 11433093, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

To a suspension of ketone from EXAMPLE 1, step 3 in MeOH (0.15M) at 0° C. was condensed NH3 (30% volume) and added methyl propiolate (6 eq). The reaction mixture was heated in a pressure tube at 150° C. for 5 h, cooled to rt and concentrated to dryness. The residue was purified by flash chromatography (EtOH:EtOAc, 12:88) to afforded the title compound.

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated to dryness
  3. customThe residue was purified by flash chromatography (EtOH:EtOAc, 12:88)

Sources & evidence

ORD record
ord-b009417e1c4d401cb9d4ddf3351c4ae4
Source dataset
uspto-grants-2009_01
Patent number
US07482456B2

Reaction notes

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