Trifluoroacetic acid → HCID 59272456, compound

HRID 558155Notes

Reaction equation

HRID 558155 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[C:20]2[S:21][C:22]([C:24]3[C:29]([F:30])=[CH:28][N:27]=[C:26]([NH:31][CH2:32][CH2:33][N:34]4[CH:38]=[CH:37][N:36]=[N:35]4)[N:25]=3)=[CH:23][C:19]=2[CH:18]=[CH:17][CH:16]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:34]1([CH2:33][CH2:32][NH:31][C:26]2[N:25]=[C:24]([C:22]3[S:21][C:20]4[C:15]([C:10]5[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=5[CH2:8][NH2:7])=[CH:16][CH:17]=[CH:18][C:19]=4[CH:23]=3)[C:29]([F:30])=[CH:28][N:27]=2)[CH:38]=[CH:37][N:36]=[N:35]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66999944HCID 66999944, compound

Product 1

HCID 59272456HCID 59272456, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine (2-{2-[5-fluoro-2-(2-[1,2,3]triazol-1-yl-ethylamino)-pyrimidin-4-yl]-benzo[b]thiophen-7-yl}-benzyl)-carbamic acid tert-butyl ester (100 mg, 0.18 mmol) and dry TFA acid (2.0 mL) in dry DCM (2.2 mL). Stir the solution at RT for 1 h. Remove the solvent. Add DCM, wash with saturated sodium bicarbonate solution, water, and aqueous saturated sodium chloride. Separate the organic layer and dry over magnesium sulfate. Filter and concentrate in vacuo. Purify the residue by column chromatography [0.1% to 2% 2 M ammonia in methanol/DCM] to give the title compound (78 mg, 96%). MS (ES) m/z 446 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-91fb4e7aa0704fbb86360d44b44bfdf5
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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