Dimethylcarbamoyl Chloride → HCID 22648893, compound

HRID 393174Notes

Reaction equation

HRID 393174 reaction equation
[H-].[K+].[C:3]1([CH:13]2[O:19][C:18]3[CH:20]=[CH:21][CH:22]=[N:23][C:17]=3[N:16]3[CH:24]=[CH:25][CH:26]=[C:15]3[C:14]2=[O:27])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[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:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1)=[O:31]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82127Potassium hydrideHCID 11738895HCID 11738895, compound

Product 1

HCID 22648893HCID 22648893, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of potassium hydride (0.281 g, 2.45 mmol, 35% in oil) in anhydrous THF (5.0 mL) was added the the (±)-6-(1-naphthyl)pyrrolo[1,2-d]pyrido[3,2-b][1,4]oxazepin-7(6H)-one (800 mg, 2.45 mmol) dissolved in anhydrous THF (5 mL). The reaction mixture was stirred at rt for 2 h, and then dimethylcarbamoyl chloride (0.303 g, 2.82 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-13 in 78% yield. IR (neat) 1725 cm−1; 1HNMR (CDCl3) δ 2.61 (s, 3 H), 2.70 (s, 3 H), 6.44 (m, 2 H), 7.10 (m, 2 H), 7.41-7.59 (m, 4 H), 7.62-7.90 (m, 3 H), 8.12 (m, 1 H), 8.25 (m, 1 H).

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-13 in 78% yield

Sources & evidence

ORD record
ord-834b36e364e347dbb51424eefe2380fc
Source dataset
uspto-grants-2004_10
Patent number
US06806267B1

Reaction notes

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