Phosgene → HCID 10179168, compound

HRID 982869Notes

Reaction equation

HRID 982869 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]1[S:17][CH2:16][CH2:15][N:14]=[C:13]([C:18]2[C:19](=[O:26])[O:20][C:21]([CH3:25])=[CH:22][C:23]=2[OH:24])[CH2:12]1.C(N(C(C)C)CC)(C)C.[C:36](Cl)(Cl)=[O:37]>C(Cl)CCl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]1[CH:12]=[C:13]2[C:18]3[C:19](=[O:26])[O:20][C:21]([CH3:25])=[CH:22][C:23]=3[O:24][C:36](=[O:37])[N:14]2[CH2:15][CH2:16][S:17]1

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 1354004393-(7-(2,4-Dimethoxyphenyl)-2,3,6,7-tetrahydro-(1,4)thiazepin-5-yl)-4-hydroxy-6-methylpyran-2-one

Product 1

HCID 10179168HCID 10179168, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

3-[7-(2,4-Dimethoxyphenyl)-2,3,6,7-tetrahydro-[1,4]thiazepin-5-yl]-4-hydroxy-6-methyl-pyran-2-one (63 mg, 0.168 mmol), prepared as in Reference 5, was dissolved in ethylene dichloride (2 mL) and then 4-(dimethylamino)pyridine (0.020 g), di-iso-propylethylamine (0.5 mL) and phosgene (0.4 ml, 2 M in toluene) were added at room temperature. The reaction was monitored by analytical HPLC. After stirring at room temperature for 30 minutes, the solvent was removed in vacuo. Product was purified by HPLC (RPC18 column, 2-70% acetonitrile/water containing 0.1% HCl) to provide 10-(2,4-dimethoxy-phenyl)-3-methyl-7,8-dihydro-10H-2,5-dioxa-9-thia-6a-aza-cyclohepta[a]naphthalene-1,6-dione (20 mg) as an off-white powder. LCMS: M+ 401.0.

Workup

  1. customthe solvent was removed in vacuo
  2. customProduct was purified by HPLC (RPC18 column, 2-70% acetonitrile/water containing 0.1% HCl)

Sources & evidence

ORD record
ord-44abfc6f37e448b6bf6ee0ac8fbfab91
Source dataset
uspto-grants-2005_03
Patent number
US06861419B2

Reaction notes

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