Diisopropylethylamine → HCID 178454316, compound

HRID 491811Notes

Reaction equation

HRID 491811 reaction equation
Cl.Cl.[O:3]([CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]=3)=[O:17])=[C:13]([NH:26][C:27]([C@H:29]3[CH2:34][CH2:33][C@H:32]([N:35]4[CH2:39][CH2:38][CH2:37][C:36]4=[O:40])[CH2:31][CH2:30]3)=[O:28])[C:12]=2[CH:41]=1)N.C(N(CC)C(C)C)(C)C.[C:51]([O:55][C:56]([NH:58][C:59]([N:68]1C=CC=N1)=[N:60][C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])=[O:57])([CH3:54])([CH3:53])[CH3:52]>CN(C)C=O>[C:64]([O:63][C:61]([N:60]([O:3][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]=3)=[O:17])=[C:13]([NH:26][C:27]([C@H:29]3[CH2:30][CH2:31][C@H:32]([N:35]4[CH2:39][CH2:38][CH2:37][C:36]4=[O:40])[CH2:33][CH2:34]3)=[O:28])[C:12]=2[CH:41]=1)[C:59]([NH:58][C:56]([O:55][C:51]([CH3:52])([CH3:53])[CH3:54])=[O:57])=[NH:68])=[O:62])([CH3:65])([CH3:66])[CH3:67]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidineHCID 178478863HCID 178478863, compound

Product 1

HCID 178454316HCID 178454316, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Trans-5-(2-aminoxyethoxy)-3-[4-(2-oxopyrrolidin-1-yl)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide dihydrochloride (90 mg) obtained in Example 183 is dissolved in N,N-dimethyl formamide (3 ml), and thereto are added N,N-diisopropylethylamine (38 μl) and N,N′-bis(t-butoxycarbonyl)-1H-pyrazole-1-carboxamidine (57 mg), and the mixture is stirred at room temperature for one day. The reaction solution is concentrated under reduced pressure, and the residue is poured into water, and extracted with chloroform. The organic layer is dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1, then ethyl acetate) to give trans-5-{2-[N,N′-bis(t-butoxycarbonyl)-guanidinoxy]ethoxy}-3-[4-(2-oxopyrrolidin-1-yl)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (82 mg).

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. additionthe residue is poured into water
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe resulting residue is purified by NH-silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-c1750e5f736b495f9b08cb060ef7b802
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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