Trifluoroacetic acid → (4-(3-(azetidin-3-yl)pyrazin-2-yloxy)phenyl)(1H-benzo[d]imidazol-2-yl)methanone

HRID 887481Notes

Reaction equation

HRID 887481 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:35]=[CH:34][C:15]([O:16][C:17]2[C:18]([CH:23]3[CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24]3)=[N:19][CH:20]=[CH:21][N:22]=2)=[CH:14][CH:13]=1)=[O:11].FC(F)(F)C(O)=O>C(Cl)Cl>[NH:25]1[CH2:26][CH:23]([C:18]2[C:17]([O:16][C:15]3[CH:34]=[CH:35][C:12]([C:10]([C:2]4[NH:1][C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=5[N:3]=4)=[O:11])=[CH:13][CH:14]=3)=[N:22][CH:21]=[CH:20][N:19]=2)[CH2:24]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59327110tert-butyl 3-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)azetidine-1-carboxylate

Product 1

HCID 59351448(4-(3-(azetidin-3-yl)pyrazin-2-yloxy)phenyl)(1H-benzo[d]imidazol-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)azetidine-1-carboxylate (175 mg, 0.371 mmol) in CH2Cl2 (1 mL) is added 2,2,2-trifluoroacetic acid (1.0 mL). The reaction was stirred at rt 1 h. The solution was concentrated and CH2Cl2 (5 mL) and saturated NaHCO3 (0.5 mL) was added. MgSO4 was added to remove water and the solution filtered and concentrated to give the crude amine as a dark green oil which was carried on to the next step without purification. (Note: An insoluble solid crashed out during the extraction, which later was identified as the desired crude amine product, which is sparingly soluble in CH2Cl2, but soluble in THF. The insoluble solid from the extraction was dissolved in THF, dried (MgSO4), concentrated, and combined with the material from aqueous extraction and carried on into the next step.

Workup

  1. concentrationThe solution was concentrated
  2. additionCH2Cl2 (5 mL) and saturated NaHCO3 (0.5 mL) was added
  3. additionMgSO4 was added
  4. customto remove water
  5. filtrationthe solution filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b319e95007e94679a72b301d3db0c917
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

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