Ammonia → HCID 59349647, compound

HRID 2090223Notes

Reaction equation

HRID 2090223 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:5]=[CH:6][NH:7][C:8](=[O:31])[C:9]=2[CH:10]([C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:28]=2[O:27][C:26]([CH3:29])=[CH:25][C:24]3=[O:30])[C:11]=1[C:12](OCCC#N)=[O:13].[CH2:32]1[CH2:36]OCC1.C(N1C=CN=C1)([N:39]1C=CN=C1)=O.N>ClCCl.CO.C(OCC)(=O)C>[CH2:36]([O:31][C:8]1[N:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]([C:19]1[CH:20]=[CH:21][CH:22]=[C:23]3[C:28]=1[O:27][C:26]([CH3:29])=[CH:25][C:24]3=[O:30])[C:11]([C:12]([NH2:39])=[O:13])=[C:2]([CH3:1])[NH:3]2)[CH3:32]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 68601724HCID 68601724, compound

Product 1

HCID 59349647HCID 59349647, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

155 mg (0.395 mmol) of the compound from Example 31A are introduced into 10 ml of THF and, after addition of 80.1 mg (0.494 mmol) of 1,1′-carbonyldiimidazole, stirred at room temperature overnight. A TLC check (silica gel; mobile phase: ethyl acetate or dichloromethane/methanol 9:1) shows complete conversion. The volatile components are removed in a rotary evaporator, and the residue is taken up in 3 ml of DMF. Then 553 mg of ammonia (28% by weight solution in water, 3.95 mmol) are added, and the reaction mixture is heated at 100° C. for 10 min. The solvent is removed under reduced pressure, and the residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5). 30 mg (19% of theory) of the title compound are obtained.

Workup

  1. customThe volatile components are removed in a rotary evaporator
  2. temperaturethe reaction mixture is heated at 100° C. for 10 min
  3. customThe solvent is removed under reduced pressure
  4. customthe residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5)

Sources & evidence

ORD record
ord-6ee0242913904acc8b2710524f9b7e7a
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

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