Ethyl chloroformate → HCID 69122753, compound

HRID 2064095Notes

Reaction equation

HRID 2064095 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:12][CH2:11][CH:10]([NH:13][C:14]3[C:15]([NH2:26])=[CH:16][CH:17]=[C:18]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])[CH:19]=3)[CH2:9][CH2:8]2)[CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[Cl:36][C:37](OCC)=[O:38]>O1CCCC1>[ClH:36].[O:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:8][CH2:9][CH:10]([N:13]3[C:14]4[CH:19]=[C:18]([O:20][CH2:21][C:22]([F:24])([F:23])[F:25])[CH:17]=[CH:16][C:15]=4[NH:26][C:37]3=[O:38])[CH2:11][CH2:12]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 59863015HCID 59863015, compound

Product 1

HCID 69122753HCID 69122753, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

A stirred solution of N2-[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]-4-[(2,2,2-trifluoroethyl)oxy]-1,2-benzenediamine (D57, 95 mg, 0.25 mmol) in tetrahydrofuran (5 ml) at room temperature under argon was treated with N,N-diisopropylethylamine (100 mg, 0.78 mmol) followed by ethyl chloroformate (33 mg, 0.30 mmol) and maintained for 3 days. The mixture was concentrated under vacuum and the residue treated with dimethylformamide (5 ml) and heated at 150° C. under argon for 7 hrs. The solution was concentrated under vacuum and the residue treated with 10% Na2CO3 solution and extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated under vacuum to leave a brown oil, which was purified by Mass-Directed Automated HPLC to afford the title compound as a white solid. This was converted to its HCl salt and isolated as a beige solid (30 mg, 29%).

Workup

  1. temperaturemaintained for 3 days
  2. concentrationThe mixture was concentrated under vacuum
  3. additionthe residue treated with dimethylformamide (5 ml)
  4. concentrationThe solution was concentrated under vacuum
  5. additionthe residue treated with 10% Na2CO3 solution
  6. extractionextracted with ethyl acetate
  7. dry with materialThe extract was dried (Na2SO4)
  8. concentrationconcentrated under vacuum
  9. customto leave a brown oil, which
  10. customwas purified by Mass-Directed Automated HPLC

Sources & evidence

ORD record
ord-e8614c07428245a2b0c2724cd835aafa
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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