Trifluoroacetic acid → HCID 25120566, compound

HRID 1640929Notes

Reaction equation

HRID 1640929 reaction equation
[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]4[C:20]([C:24]5[CH:29]=[C:28]([Cl:30])[N:27]=[CH:26][C:25]=5[CH:31]([N:33](C)[C:34](=O)OC(C)(C)C)[CH3:32])=[CH:21][CH:22]=[CH:23][C:17]=4[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C:15]3[S:19][C:18]4[C:20]([C:24]5[C:25]([CH:31]([NH:33][CH3:34])[CH3:32])=[CH:26][N:27]=[C:28]([Cl:30])[CH:29]=5)=[CH:21][CH:22]=[CH:23][C:17]=4[CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86641880HCID 86641880, compound

Product 1

HCID 25120566HCID 25120566, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine tert-butyl 1-(4-(2-(2-(2-(1H-1,2,3-triazol-1-yl)ethylamino)pyrimidin-4-yl)benzo[b]thiophen-7-yl)-6-chloropyridin-3-yl)ethyl(methyl)carbamate (300 mg, 0.5 mmol) and dry TFA (2.0 mL) in dry DCM (6 mL). Stir the solution at RT for 1 h. Dilute the resulting residue with DCM and wash with saturated sodium bicarbonate solution, water, and saturated aqueous sodium chloride. Separate the organic layer and dry over magnesium sulfate. Filter and concentrate in vacuo to give a residue. Purify the residue by column chromatography [0.1% to 2% 2 M ammonia in methanol/DCM] to afford the title compound (175 mg, 70%). MS (ES) m/z 491 [M+1]+.

Workup

  1. washwash with saturated sodium bicarbonate solution, water, and saturated aqueous sodium chloride
  2. customSeparate the organic layer
  3. dry with materialdry over magnesium sulfate
  4. filtrationFilter
  5. concentrationconcentrate in vacuo
  6. customto give a residue
  7. customPurify the residue by column chromatography [0.1% to 2% 2 M ammonia in methanol/DCM]

Sources & evidence

ORD record
ord-50d669c0e442443f8973aee74daee068
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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