HCID 18320690, compound → HCID 18320704, compound

HRID 1699527Notes

Reaction equation

HRID 1699527 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([C:25](=O)[CH:26]([NH:30][C:31]([NH:33][C:34]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[N:36]([CH2:43][CH2:44][CH3:45])[CH:35]=2)=[O:32])[C:27]([NH2:29])=[O:28])=[CH:17]1>FC(F)(F)S([O-])(=O)=O.[Sc+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.CO>[C:27]([C:26]1[NH:30][C:31](=[O:32])[N:33]([C:34]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[N:36]([CH2:43][CH2:44][CH3:45])[CH:35]=2)[C:25]=1[C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:16]([CH2:15][CH2:14][CH2:13][CH2:12][N:3]2[C:4](=[O:11])[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]2=[O:1])[CH:17]=1)(=[O:28])[NH2:29]

Participants

4

Reactant 1

HCID 18320690HCID 18320690, compound

Product 1

HCID 18320704HCID 18320704, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.06 g (0.1 mmol) of the compound of step d), 2 ml of methanol, and a catalytic amount of scandium trifluoromethanesulfonate was heated to 105° C. for 4 hours. The reaction mixture was allowed to cool, the solvent was evaporated, and the residual purified by chromatography on silica (CH2Cl2:MeOH 97:3) to give 54 mg (93%) of the sub-title amide.

Workup

  1. temperatureto cool
  2. customthe solvent was evaporated
  3. customthe residual purified by chromatography on silica (CH2Cl2:MeOH 97:3)

Sources & evidence

ORD record
ord-f86a4adbf8b04b118ac1982d8ffa19c8
Source dataset
uspto-grants-2002_02
Patent number
US06346625B1

Reaction notes

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