Trifluoroacetic acid → HCID 67280477, compound

HRID 1958159Notes

Reaction equation

HRID 1958159 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][C:15]1[CH:20]=[N:19][C:18]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)=[C:17]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[N:16]=1)(C)(C)C>>[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([C:17]2[N:16]=[C:15]([NH2:14])[CH:20]=[N:19][C:18]=2[O:21][CH:22]2[CH2:23][CH2:25][CH2:24]2)=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67280665HCID 67280665, compound

Product 1

HCID 67280477HCID 67280477, compoundYield 13.3%

Procedure

TFA (14.8 g, 10 mL, 130 mmol) was added to [6-(4-chloro-phenyl)-5-cyclopropylmethoxy-pyrazin-2-yl]-carbamic acid tert-butyl ester (example 50b, 1.365 g, 3.63 mmol). The resulting yellow solution was stirred at room temperature for 1 h. The solvent was evaporated and the residue was partitioned between ethyl acetate and 1M Na2CO3 solution; the organic phases were combined, dried with MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 100g, 10% to 50% ethyl acetate in heptane; then ethyl acetate/methanol 9/1 to give 0.133 g (13%) of the title compound (by rearrangement) as yellow oil; MS (EI) 276.1 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate and 1M Na2CO3 solution
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography (silica gel, 100g, 10% to 50% ethyl acetate in heptane

Sources & evidence

ORD record
ord-0ee87bb5ec9447bea681cd71d9b911e8
Source dataset
uspto-grants-2013_04
Patent number
US08410107B2

Reaction notes

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