Sodium Carbonate → 7-(4-benzylpiperazin-1-yl)-3-bromo-9H-carbazole-1-carboxamide

HRID 2410915Notes

Reaction equation

[NH2:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[C:8]([Br:18])[CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.Cl.[CH2:20]([N:27]([CH2:31][CH2:32]Cl)[CH2:28][CH2:29]Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[CH2:20]([N:27]1[CH2:31][CH2:32][N:1]([C:2]2[CH:14]=[C:13]3[C:5]([C:6]4[CH:7]=[C:8]([Br:18])[CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]=4[NH:12]3)=[CH:4][CH:3]=2)[CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

7-Amino-3-bromo-9H-carbazole-1-carboxamide 470B (400 mg, 1.315 mmol), N-benzyl-2-chloro-N-(2-chloroethyl)ethanamine hydrochloride (707 mg, 2.63 mmol) and sodium carbonate (697 mg, 6.58 mmol) were mixed in DMF (8 mL) in a sealed microwave vial. The vial was degassed and filled with N2. The mixture was heated at 80° C. for 16 hrs in an oil bath. The mixture was then heated in microwave at 200 C for 1 hr. The mixture was purified using preparative HPLC to give titled product. MS (ESI) m/z 463.07 (M+H)+.

Workup

customThe vial was degassed
additionfilled with N2
temperatureThe mixture was then heated in microwave at 200 C for 1 hr
customThe mixture was purified

Sources & evidence

ORD record: ord-f7d6ba6efa084d298a44774454ab5a91
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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