Pyridine → HCID 44231033, compound

HRID 1907264Notes

Reaction equation

HRID 1907264 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][CH2:9][CH2:10][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[OH:12])[CH:5]=[CH:6][CH:7]=1.Cl[C:21](Cl)([O:23]C(=O)OC(Cl)(Cl)Cl)Cl.CCN(C(C)C)C(C)C.N1C=CC=CC=1>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:9][CH2:10][CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[O:12][C:21]2=[O:23])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 58200033HCID 58200033, compound

Product 1

HCID 44231033HCID 44231033, compoundYield 164%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Half of the crude 3-(3-bromophenylamino)-1-(2-chlorophenyl)propan-1-ol (0.074 mmol) was mixed with triphosgene (7.5 mg, 0.34 equiv), i-Pr2NEt (26 μL, 2 equiv), pyridine (30 μL, 5 equiv) and acetonitrile (5 mL). The mixture was put in the microwave oven for 30 min at 110° C. LC-MS found the reaction completed. The mixture was concentrated, redissolved in EtOAc (5 mL), washed with 1% aq HCl (2×2 mL), concentrated and purified by preparative HPLC to afford 3-(3-bromo-phenyl)-6-(2-chloro-phenyl)-[1,3]oxazinan-2-one (15.2 mg). LC-MS (3 min) tR=1.86 min., m/z 368,369(M+1). 1H NMR (CDCl3) δ 7.63(d, 1H), 7.56 (s, 1H), 7.43-7.26 (m, 6H), 5.83 (d, 1H), 3.88 (q, 1H), 3.67 (m, 1H), 2.55 (d, 1H), 2.17 (m, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionredissolved in EtOAc (5 mL)
  3. washwashed with 1% aq HCl (2×2 mL)
  4. concentrationconcentrated
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-7dfc88401fc84a4392e7457181b2d036
Source dataset
uspto-grants-2013_12
Patent number
US08598160B2

Reaction notes

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