Diethylamine → HCID 67406587, compound

HRID 1174273Notes

Reaction equation

HRID 1174273 reaction equation
C1C2C(C[O:15][C:16]([N:18]([CH2:34][C:35]3[N:39](C)[C:38]4[CH:41]=[CH:42][CH:43]=[CH:44][C:37]=4[N:36]=3)[CH2:19][CH2:20][NH:21][C@@H:22]([C@@H:30]([CH3:33])[CH2:31][CH3:32])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=O)C3C(=CC=CC=3)C=2C=CC=1.[CH2:45](NCC)C.[N+](C1C=CC(OC(=O)OC2C=CC([N+]([O-])=O)=CC=2)=CC=1)([O-])=O>CN(C)C=O.ClCCCl>[CH3:33][C@@H:30]([CH2:31][CH3:32])[C@H:22]([N:21]1[CH2:20][CH2:19][N:18]([CH2:34][C:35]2[N:39]([CH3:45])[C:38]3[CH:41]=[CH:42][CH:43]=[CH:44][C:37]=3[N:36]=2)[C:16]1=[O:15])[C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 78756Bis(4-nitrophenyl) carbonateHCID 67407693HCID 67407693, compound

Product 1

HCID 67406587HCID 67406587, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of the product of Example 96A (0.81 mmol) in N,N-dimethylformamide (5 mL) was treated with diethylamine (0.8 mL), stirred at 25° C. for 2 hours and concentrated. A solution of the residue in 1,2-dichloroethane (16 mL) was treated with bis-(p-nitrophenyl)carbonate (0.296 g, 0.973 mmol), stirred at 60° C. for 16 hours and concentrated. The residue was chromatographed on silica gel, eluting with 0-100% ethyl acetate/dichloromethane to give the title compound (0.192 g, 59% yield).

Workup

  1. concentrationconcentrated
  2. stirringstirred at 60° C. for 16 hours
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel
  5. washeluting with 0-100% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-91b065097f77415395ce4cc7c9b01513
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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