Trifluoroacetic acid → HCID 136041769, compound

HRID 880128Notes

Reaction equation

HRID 880128 reaction equation
FC(F)(F)C(O)=O.[N:8]1([C:14]2[N:15]=[C:16]([CH2:21][C:22]([NH:24][C:25]3[CH:33]=[CH:32][CH:31]=[C:30]4[C:26]=3[CH:27]=[CH:28][N:29]4C(OC(C)(C)C)=O)=[O:23])[NH:17][C:18](=[O:20])[CH:19]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1>ClCCl>[NH:29]1[C:30]2[C:26](=[C:25]([NH:24][C:22](=[O:23])[CH2:21][C:16]3[NH:17][C:18](=[O:20])[CH:19]=[C:14]([N:8]4[CH2:13][CH2:12][O:11][CH2:10][CH2:9]4)[N:15]=3)[CH:33]=[CH:32][CH:31]=2)[CH:27]=[CH:28]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136352205HCID 136352205, compound

Product 1

HCID 136041769HCID 136041769, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.940 ml of trifluoroacetic acid is added dropwise to a solution of 200 mg of 2-methylpropan-2-yl 4-({[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetyl}amino)-1H-indole-1-carboxylate in 8 ml of dichloromethane. After stirring at ambient temperature for 3 hours, the reaction medium is concentrated under reduced pressure, taken up with toluene and concentrated under reduced pressure. After purification by silica column chromatography, eluent: 90/10 CH2Cl2/MeOH, 48 mg of N-(1H-indol-4-yl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide are obtained, the characteristics of which are the following:

Workup

  1. concentrationthe reaction medium is concentrated under reduced pressure
  2. concentrationconcentrated under reduced pressure
  3. customAfter purification by silica column chromatography, eluent

Sources & evidence

ORD record
ord-38ff768a0c834d2bbbf55571012913d9
Source dataset
uspto-grants-2015_03
Patent number
US08993565B2

Reaction notes

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