Dimethylcarbamoyl Chloride → HCID 22648888, compound

HRID 393175Notes

Reaction equation

HRID 393175 reaction equation
[H-].[K+].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH:13]1[O:19][C:18]2[CH:20]=[CH:21][CH:22]=[N:23][C:17]=2[N:16]2[CH:24]=[CH:25][CH:26]=[C:15]2[C:14]1=[O:27].[CH3:28][N:29]([CH3:33])[C:30](Cl)=[O:31]>C1COCC1>[CH3:28][N:29]([CH3:33])[C:30]([O:27][C:14]1[C:15]2[N:16]([CH:24]=[CH:25][CH:26]=2)[C:17]2[N:23]=[CH:22][CH:21]=[CH:20][C:18]=2[O:19][C:13]=1[C:4]1[CH:5]=[CH:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:3]=1)=[O:31]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82127Potassium hydrideHCID 22648892HCID 22648892, compound

Product 1

HCID 22648888HCID 22648888, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of potassium hydride (0.211 g, 1.84 mmol, 35% in oil) in anhydrous TBF (5.0 mL) was added the the (±)-6-(2-naphthyl)pyrrolo[1,2-d]pyrido[3,2-b][1,4]oxazepin-7(6H)-one (600 mg, 1.84 mmol) dissolved in anhydrous THF (5 mL). The reaction mixture was stirred at rt for 2 h, and then dimethylcarbamoyl chloride (0.228 g, 2.12 mmol) was slowly added. After stirring for 12 h at 30° C., the solvent was removed in vacuo and the residue was dissolved in EtOAc. The organic layer was washed with brine, dried and concentrated. The residue was chromatographed (dichloromethane and hexane 1:3) to give the PBOX-43 in 76% yield. IR (neat) 1730 cm−1; 1HNMR (CDCl3) δ 2.92 (s, 3 H), 3.12 (s, 3 H), 6.44 (m, 2 H), 7.12 (m, 1 H), 7.47-7.55 (m, 3 H), 7.73-7.87 (m, 5 H), 8.24(m, 2H).

Workup

  1. stirringAfter stirring for 12 h at 30° C.
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in EtOAc
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed (dichloromethane and hexane 1:3)
  8. customto give the PBOX-43 in 76% yield

Sources & evidence

ORD record
ord-4ab596020c5c49b9982081dbed723d6a
Source dataset
uspto-grants-2004_10
Patent number
US06806267B1

Reaction notes

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