Water → HCID 25102817, compound

HRID 1672770Notes

Reaction equation

HRID 1672770 reaction equation
[CH2:1]([NH:3][C:4]1[N:5]=[CH:6][C:7]2[C:16](=[O:17])[N:15]([CH2:18][CH:19]3[CH2:24][CH2:23][N:22](C4C=NC=NC=4)[CH2:21][CH2:20]3)[CH2:14][C@H:13]3[N:9]([CH2:10][CH2:11][CH2:12]3)[C:8]=2[N:31]=1)[CH3:2].C(N(CC)C(C)C)(C)C.[O:41]1[CH:45]=[CH:44][CH:43]=[C:42]1[C:46](Cl)=[O:47].O>ClCCl>[CH2:1]([NH:3][C:4]1[N:5]=[CH:6][C:7]2[C:16](=[O:17])[N:15]([CH2:18][CH:19]3[CH2:20][CH2:21][N:22]([C:46]([C:42]4[O:41][CH:45]=[CH:44][CH:43]=4)=[O:47])[CH2:23][CH2:24]3)[CH2:14][C@H:13]3[N:9]([CH2:10][CH2:11][CH2:12]3)[C:8]=2[N:31]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 682422-Furancarbonyl chlorideHCID 81531DiisopropylethylamineHCID 67350934HCID 67350934, compound

Product 1

HCID 25102817HCID 25102817, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 32 (800 mg, 1.92 mmol) obtained in Example 32 was suspended in dichloromethane (15 mL), and the mixture was stirred at room temperature for 4 hours after adding N,N-diisopropylethylamine (1.16 mL, 6.71 mmol) and 2-furoyl chloride (226 μL, 2.30 mmol). Thereafter, water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The resulting residue was purified by silica gel column chromatography, and crystallized from diethyl ether to give the title compound (Compound 35) (601 mg, 71%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe resulting residue was purified by silica gel column chromatography
  6. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-998671f6ff8d4b55b02e695dfcdd254f
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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