2-Chloroethyl isocyanate → 4-bromo-7-(2-oxoimidazolidin-1-yl)-9H-carbazole-1-carboxamide

HRID 1811164Notes

Reaction equation

HRID 1811164 reaction equation
Br.[NH2:2][C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[C:8]([Br:19])=[CH:9][CH:10]=[C:11]([C:16]([NH2:18])=[O:17])[C:12]=3[NH:13]2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.Cl[CH2:30][CH2:31][N:32]=[C:33]=[O:34].[H-].[Na+]>CN(C=O)C.O>[Br:19][C:8]1[C:7]2[C:6]3[C:14](=[CH:15][C:3]([N:2]4[CH2:30][CH2:31][NH:32][C:33]4=[O:34])=[CH:4][CH:5]=3)[NH:13][C:12]=2[C:11]([C:16]([NH2:18])=[O:17])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 160352-Chloroethyl isocyanateHCID 24758Sodium hydrideHCID 81531DiisopropylethylamineHCID 666057197-amino-4-bromo-9H-carbazole-1-carboxamide hydrobromide

Product 1

HCID 593749934-bromo-7-(2-oxoimidazolidin-1-yl)-9H-carbazole-1-carboxamideYield 60.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 7-amino-4-bromo-9H-carbazole-1-carboxamide hydrobromide (Example 54-2, 700 mg, 1.818 mmol) and DIEA (0.381 mL, 2.182 mmol) in DMF (5 mL) was treated with 1-chloro-2-isocyanatoethane (230 mg, 2.182 mmol). After 2 h, the mixture was treated with NaH (60% in mineral oil, 582 mg, 14.54 mmol). After 10 min, the mixture was diluted with water. The precipitate was collected by filtration, dried, triturated with methanol, collected again by filtration and dried to provide 4-bromo-7-(2-oxoimidazolidin-1-yl)-9H-carbazole-1-carboxamide as a light yellow solid (410 mg, 60%). 1H NMR (400 MHz, DMSO-d6) δ 11.55 (1 H, s), 8.46 (1 H, d, J=8.80 Hz), 8.16 (1 H, br. s.), 7.92 (1 H, s), 7.77 (1 H, d, J=8.14 Hz), 7.63-7.68 (1 H, m), 7.52 (1 H, br. s.), 7.36-7.41 (1 H, m), 6.99 (1 H, s), 3.92-3.98 (2 H, m), 3.43-3.50 (2 H, m). Mass spectrum m/z 373, 375 (M+H)+.

Workup

  1. waitAfter 10 min
  2. filtrationThe precipitate was collected by filtration
  3. customdried
  4. customtriturated with methanol
  5. filtrationcollected again by filtration
  6. customdried

Sources & evidence

ORD record
ord-1fba38487491453db4bd275c3a5292fd
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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