Acetonitrile → Jnj-38893777

HRID 1186115Notes

Reaction equation

HRID 1186115 reaction equation
Cl[C:2]1[C:12]2[CH2:11][CH2:10][N:9]([C:13]3[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:16]=[CH:15][N:14]=3)[CH2:8][CH2:7][C:6]=2[N:5]=[C:4]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[N:3]=1.N1(C2N=C(O)C3CCN([C:45]4[C:50]([C:51]([F:54])([F:53])[F:52])=[CH:49][CH:48]=[CH:47][N:46]=4)CCC=3N=2)CCCCC1.O=P(Cl)(Cl)Cl.[CH3:62]C#N>CCOC(C)=O>[N:23]1([C:4]2[N:3]=[C:2]([NH:46][C:47]3[CH:48]=[CH:49][C:50]([C:51]([F:52])([F:53])[F:54])=[CH:45][CH:62]=3)[C:12]3[CH2:11][CH2:10][N:9]([C:13]4[C:18]([C:19]([F:22])([F:20])[F:21])=[CH:17][CH:16]=[CH:15][N:14]=4)[CH2:8][CH2:7][C:6]=3[N:5]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 866153064-Chloro-2-piperidin-1-yl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepineHCID 178517884HCID 178517884, compound

Product 1

HCID 16742146Jnj-38893777Yield 35%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Chloro-2-piperidin-1-yl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine. To a solution of 2-piperidin-1-yl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-ol (435 mg, 1.11 mmol) in CH3CN (9 mL) was added POCl3 (0.41 mL, 4.43 mmol). After 1.5 h at 80° C., the mixture was cooled to rt, diluted with EtOAc, and quenched slowly with satd. aq. NaHCO3. The organic layers were combined, dried (Na2SO4), and concentrated. The crude residue was purified (FCC) to give the title compound (160 mg, 35%).

Workup

  1. customquenched slowly with satd
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude residue was purified (FCC)

Sources & evidence

ORD record
ord-b47b99acc18e474e8caea6b3aff953aa
Source dataset
uspto-grants-2014_03
Patent number
US08673895B2

Reaction notes

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