Triethylamine → HCID 22711097, compound

HRID 352972Notes

Reaction equation

HRID 352972 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([S:18]([N:21]1[CH2:26][CH2:25][N:24]([C:27]([C:29]3[S:30][C:31]4[CH2:32][NH:33][CH2:34][CH2:35][C:36]=4[N:37]=3)=[O:28])[CH:23]([CH2:38][C:39]([NH:41][S:42]([CH3:45])(=[O:44])=[O:43])=[O:40])[CH2:22]1)(=[O:20])=[O:19])=[CH:12]2.C(N(CC)CC)C.[C:53](=O)([O:61]C1C=CC([N+]([O-])=O)=CC=1)[O:54][CH:55]([O:57][C:58](=[O:60])[CH3:59])[CH3:56]>C(O)C>[C:58]([O:57][CH:55]([O:54][C:53]([CH:34]1[NH:33][CH2:32][C:31]2[S:30][C:29]([C:27]([N:24]3[CH2:25][CH2:26][N:21]([S:18]([C:13]4[NH:14][C:15]5[C:11]([CH:12]=4)=[CH:10][C:9]([Cl:8])=[CH:17][CH:16]=5)(=[O:20])=[O:19])[CH2:22][CH:23]3[CH2:38][C:39]([NH:41][S:42]([CH3:45])(=[O:44])=[O:43])=[O:40])=[O:28])=[N:37][C:36]=2[CH2:35]1)=[O:61])[CH3:56])(=[O:60])[CH3:59]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 117805601-acetoxyethyl p-nitrophenyl carbonateHCID 22711201HCID 22711201, compound

Product 1

HCID 22711097HCID 22711097, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (2 ml) was dissolved N-[[4-[(5-chloroindol-2-yl)sulfonyl]-1-[(4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]piperazin-2-yl]acetyl]methanesulfonamide trifluoroacetate (97 mg), followed by the addition of triethylamine (0.63 ml) and 1-acetoxyethyl p-nitrophenyl carbonate (110 mg). The resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure. Methylene chloride was added to the residue. The resulting mixture was washed with water, dried over anhydrous sodium sulfate and distilled to remove the solvent. The residue was purified by chromatography on a silica gel column (methylene chloride:methanol=50:1), whereby the title compound (50 mg) was obtained as a colorless foam.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionMethylene chloride was added to the residue
  3. washThe resulting mixture was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue was purified by chromatography on a silica gel column (methylene chloride:methanol=50:1), whereby the title compound (50 mg)
  8. customwas obtained as a colorless foam

Sources & evidence

ORD record
ord-9f25f77afe4e4b8393e4d04dfcfee96e
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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