Water → HCID 178505002, compound

HRID 491816Notes

Reaction equation

HRID 491816 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([NH:21][C:22]([C@H:24]3[CH2:29][CH2:28][C@H:27]([N:30]4[CH2:34][CH2:33][CH2:32][C:31]4=[O:35])[CH2:26][CH2:25]3)=[O:23])=[C:9]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][N:15]=3)=[O:12])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:36][S:37](Cl)(=[O:39])=[O:38].O>N1C=CC=CC=1>[CH3:36][S:37]([NH:1][C:2]1[C:7]2[C:8]([NH:21][C:22]([C@H:24]3[CH2:25][CH2:26][C@H:27]([N:30]4[CH2:34][CH2:33][CH2:32][C:31]4=[O:35])[CH2:28][CH2:29]3)=[O:23])=[C:9]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][N:15]=3)=[O:12])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1)(=[O:39])=[O:38]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chloride2×HCID 178507477HCID 178507477, compound

Product 1

HCID 178505002HCID 178505002, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Trans-4-amino-3-[4-(2-oxopyrrolidin-1-yl)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (27 mg) obtained in Example 426 is dissolved in pyridine (2 ml), and thereto is added methanesulfonyl chloride (7 μl) under ice-cooling. The mixture is stirred at room temperature overnight, and thereto are further added pyridine (3 ml) and methanesulfonyl chloride (500 μl) under ice-cooling. The mixture is stirred at room temperature for 6 hours. Water is added to the reaction solution, and the mixture is extracted with chloroform. The solvent is evaporated under reduced pressure, and the resulting residue is purified by silica gel column chromatography (eluent: chloroform, then chloroform/methanol=9/1) to give the title compound (21.2 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringThe mixture is stirred at room temperature for 6 hours
  4. extractionthe mixture is extracted with chloroform
  5. customThe solvent is evaporated under reduced pressure
  6. customthe resulting residue is purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-dce67aff05564d8597c861d9c9f14f4a
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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