Potassium Iodide → HCID 178500409, compound

HRID 491809Notes

Reaction equation

HRID 491809 reaction equation
Cl.Cl.[NH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([NH:12][C:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[O:15][C:14]=2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=2)=[O:23])=[O:11])[CH2:6][CH2:5]1.Br[CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38].C(N(CC)C(C)C)(C)C.[I-].[K+]>CN(C)C(=O)C.C(OCC)(=O)C>[CH3:40][O:39][C:37]([CH2:36][CH2:35][CH2:34][CH2:33][NH:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([NH:12][C:13]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[O:15][C:14]=2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=2)=[O:23])=[O:11])[CH2:6][CH2:5]1)=[O:38]

Participants

7

Reactant 4

HCID 4875Potassium Iodide2×HCID 79557Methyl 5-bromovalerate2×HCID 81531Diisopropylethylamine2×HCID 178478721HCID 178478721, compound

Product 1

HCID 178500409HCID 178500409, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

Trans-3-(4-aminocyclohexylcarbonylamino)-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide dihydrochloride (300 mg) obtained in Example 219 is suspended in N,N-dimethylacetamide (5 ml), and thereto are added methyl 5-bromovalerate (106 μl), N,N-diisopropylethylamine (537 μl), and potassium iodide (111 mg), and the mixture is stirred at 100° C. for 24 hours. Methyl 5-bromovalerate (106 μl), N,N-diisopropylethylamine (537 μl) and potassium iodide (111 mg) are further added thereto, and the mixture is stirred at 100° C. for 12 hours. The reaction solution is diluted with ethyl acetate, and washed successively with a saturated aqueous sodium hydrogen carbonate solution, water, a saturated brine, and dried over sodium sulfate. The solvent is evaporated under reduced pressure, and the resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1, then ethyl acetate) to give trans-3-[4-(4-methoxycarbonylbutylamino)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)-benzofuran-2-carboxamide (101 mg).

Workup

  1. stirringthe mixture is stirred at 100° C. for 12 hours
  2. washwashed successively with a saturated aqueous sodium hydrogen carbonate solution, water
  3. dry with materiala saturated brine, and dried over sodium sulfate
  4. customThe solvent is evaporated under reduced pressure
  5. customthe resulting residue is purified by NH-silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-a30d33ea7bee41a79dd0e566e7c2b8a0
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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