Phosphorus oxychloride → HCID 58972713, compound

HRID 1186111Notes

Reaction equation

HRID 1186111 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:25]>CC#N.CCOC(C)=O>[Cl:25][C:16]1[C:13]2[CH2:14][CH2:15][N:9]([C:4]3[C:3]([C:2]([F:22])([F:21])[F:1])=[CH:8][CH:7]=[CH:6][N:5]=3)[CH2:10][CH2:11][C:12]=2[N:19]=[CH:18][N:17]=1

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517910HCID 178517910, compound

Product 1

HCID 58972713HCID 58972713, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

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-469b5f69cc574bfb97bc15ab247b8af8
Source dataset
uspto-grants-2014_03
Patent number
US08673895B2

Reaction notes

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