Hydrogen Bromide → HCID 178482084, compound

HRID 491775Notes

Reaction equation

HRID 491775 reaction equation
C(O[C:9]([N:11]([C:13]1[CH:14]=[CH:15][C:16]2[O:20][C:19]([C:21]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][N:25]=3)=[O:22])=[C:18]([NH:31][C:32]([C@H:34]3[CH2:39][CH2:38][C@H:37]([N:40]([CH3:42])[CH3:41])[CH2:36][CH2:35]3)=[O:33])[C:17]=2[CH:43]=1)C)=O)C1C=CC=CC=1.Br.C(OCC)C>C(O)(=O)C>[CH3:42][N:40]([CH3:41])[C@H:37]1[CH2:36][CH2:35][C@H:34]([C:32]([NH:31][C:18]2[C:17]3[CH:43]=[C:13]([NH:11][CH3:9])[CH:14]=[CH:15][C:16]=3[O:20][C:19]=2[C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][N:25]=2)=[O:22])=[O:33])[CH2:39][CH2:38]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 178485992HCID 178485992, compound

Product 1

HCID 178482084HCID 178482084, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To trans-5-[N-(benzyloxycarbonyl)-N-methylamino]-3-[4-(dimethylamino)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (100 mg) obtained in Example 22 is added 30% hydrogen bromide in acetic acid (2 ml), and the mixture is stirred at room temperature for 2 hours. To the reaction solution is added diethyl ether (20 ml), and the precipitates are collected by filtration, and suspended in a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer is washed with a saturated brine, dried over sodium sulfate, and the solvent is evaporated under reduced pressure to give trans-3-[4-(dimethylamino)cyclohexylcarbonylamino]-5-methylamino-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide. Subsequently, this product is dissolved in ethanol, and treated with 4N hydrogen chloride in ethyl acetate to give the title compound (88 mg).

Workup

  1. filtrationthe precipitates are collected by filtration
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed with a saturated brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-f5a9a635b9a84cd38db535ed94b8adfd
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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