Water → HCID 11433704, compound

HRID 1455651Notes

Reaction equation

HRID 1455651 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]([C:24]4[S:28][C:27]([C:29](O)=O)=[N:26][C:25]=4[C:32]4[CH:37]=[CH:36][C:35]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:34][CH:33]=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].C1N=CN(C(N2C=NC=C2)=O)C=1.[C:54](=[N:57][OH:58])([NH2:56])[CH3:55].O>CN(C=O)C>[CH3:3][C:2]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[S:28][C:27]([C:29]5[O:58][N:57]=[C:54]([CH3:55])[N:56]=5)=[N:26][C:25]=4[C:32]4[CH:33]=[CH:34][C:35]([S:38]([CH3:41])(=[O:39])=[O:40])=[CH:36][CH:37]=4)[CH:19]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([S:4]([CH3:7])(=[O:5])=[O:6])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 30926N-HydroxyacetamidineHCID 682631,1'-CarbonyldiimidazoleHCID 68954788HCID 68954788, compound

Product 1

HCID 11433704HCID 11433704, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of acid from step 1 in DMF (0.05M) was added CDI (1.1 eq) and, after 5 min, acetamidoxime (1.1 eq). The reaction mixture was stirred at rt for 1 h and 18 h at 110° C. The reaction mixture was cooled to rt and poured into water. The residue was purified by flash chromatography (toluene:EtOAc, 45:55) to afforded the title compound and decarboxylated analog EXAMPLE 73 (more polar product).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customThe residue was purified by flash chromatography (toluene:EtOAc, 45:55)

Sources & evidence

ORD record
ord-8f385da5af7043f09a0b8cc676182895
Source dataset
uspto-grants-2009_01
Patent number
US07482456B2

Reaction notes

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