Trifluoroacetic acid → HCID 25120562, compound

HRID 1640926Notes

Reaction equation

HRID 1640926 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][C:10]1[CH:11]=[N:12][C:13]([F:40])=[CH:14][C:15]=1[C:16]1[C:21]2[S:22][C:23]([C:25]3[C:30]([F:31])=[CH:29][N:28]=[C:27]([NH:32][CH2:33][CH2:34][N:35]4[CH:39]=[CH:38][N:37]=[N:36]4)[N:26]=3)=[CH:24][C:20]=2[CH:19]=[CH:18][CH:17]=1)C)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:35]1([CH2:34][CH2:33][NH:32][C:27]2[N:26]=[C:25]([C:23]3[S:22][C:21]4[C:16]([C:15]5[C:10]([CH2:9][NH:7][CH3:6])=[CH:11][N:12]=[C:13]([F:40])[CH:14]=5)=[CH:17][CH:18]=[CH:19][C:20]=4[CH:24]=3)[C:30]([F:31])=[CH:29][N:28]=2)[CH:39]=[CH:38][N:37]=[N:36]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66738246HCID 66738246, compound

Product 1

HCID 25120562HCID 25120562, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine (6-fluoro-4-{2-[5-fluoro-2-(2-[1,2,3]triazol-1-yl-ethylamino)-pyrimidin-4-yl]-benzo[b]thiophen-7-yl}-pyridin-3-ylmethyl)-methyl-carbamic acid tert-butyl ester (0.30 g, 0.51 mmol) and dry TFA (2.0 mL) and dry DCM (2.2 mL). Stir at RT for 1 h. Evaporate off the solvents. 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 the crude product. Purify by column chromatography [0.1% to 2% 2 M ammonia in methanol/DCM] to afford the title compound (0.20 g, 83%). MS (ES) m/z 479 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-d4555c305f9a49b2bf85b6f63736637c
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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