Ethyl Acetate → HCID 24782891, compound

HRID 1485340Notes

Reaction equation

HRID 1485340 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[C:4]([N:9]2[CH2:15][CH2:14][C:13]3[C:16](O)=[N:17][CH:18]=[N:19][C:12]=3[CH2:11][CH2:10]2)=[N:5][CH:6]=[CH:7][CH:8]=1.O=P(Cl)(Cl)Cl.CCO[C:31]([CH3:33])=O>CC#N>[C:3]([C:31]1[CH:33]=[CH:13][C:12]([NH:19][C:16]2[C:13]3[CH2:14][CH2:15][N:9]([C:4]4[C:3]([C:2]([F:22])([F:21])[F:1])=[CH:8][CH:7]=[CH:6][N:5]=4)[CH2:10][CH2:11][C:12]=3[N:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:8])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 178517910HCID 178517910, compound

Product 1

HCID 24782891HCID 24782891, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-ol (185 mg, 0.60 mmol) in CH3CN (2 mL) was added POCl3 (0.11 mL, 1.19 mmol). The reaction mixture was heated at 90° C. for 2 h. The mixture was cooled to rt, diluted with EtOAc, and quenched slowly with saturated (satd.) aq. NaHCO3. The combined organic layers were dried (Na2SO4) and concentrated. The crude residue was purified (FCC) to give the title compound (65 mg, 33%).

Workup

  1. temperatureThe mixture was cooled to rt
  2. customquenched slowly with saturated (satd.) aq. NaHCO3
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified (FCC)

Sources & evidence

ORD record
ord-ada1a96d45eb4c74bf866b1ff774a8b0
Source dataset
uspto-grants-2016_08
Patent number
US09422293B2

Reaction notes

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