Dimethylformamide → HCID 70195540, compound

HRID 481949Notes

Reaction equation

HRID 481949 reaction equation
Cl.Cl.Cl.[N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([N:16]3[CH2:20][C@H:19]([CH2:21][NH2:22])[O:18][C:17]3=[O:23])=[N:14][CH:15]=2)[CH:5]=1.CN(C=O)C.[N+:29]([C:32]([CH3:41])=[CH:33]NC1C=CC=CN=1)([O-:31])=[O:30]>O>[N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([N:16]3[CH2:20][C@@H:19]([CH:21]([CH:33]=[C:32]([N+:29]([O-:31])=[O:30])[CH3:41])[NH2:22])[O:18][C:17]3=[O:23])=[N:14][CH:15]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 70193777HCID 70193777, compoundHCID 70195308HCID 70195308, compound

Product 1

HCID 70195540HCID 70195540, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 mg (0.37 mmol) of the compound from Example XXVIII (free base; prepared by dissolving in water, NH3(aq) addition to pH 11, extraction with CH2Cl2, drying over MgSO4 and concentrating) are initially introduced into 1 ml of DMF under argon and 200 mg (1.11 mmol) of 2-(2-nitro-prop-1-en-1-yl-amino)-pyridine are added and the mixture is stirred overnight. It is treated with water, extracted 3× with ethyl acetate, and the organic phase is washed with satd. NaCl solution and dried over MgSO4. It is concentrated and the residue is purified by column chromatography on silica gel (eluent CH2Cl2 :MeOH=100:5). 126 mg (96% of theory) of the title compound are obtained.

Workup

  1. extractionextracted 3× with ethyl acetate
  2. washthe organic phase is washed with satd
  3. dry with materialNaCl solution and dried over MgSO4
  4. concentrationIt is concentrated
  5. customthe residue is purified by column chromatography on silica gel (eluent CH2Cl2 :MeOH=100:5)

Sources & evidence

ORD record
ord-67b36af33cc04979aefe93ad273ede23
Source dataset
uspto-grants-1998_08
Patent number
US05792765

Reaction notes

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