Ammonia → HCID 59349661, compound

HRID 2090224Notes

Reaction equation

HRID 2090224 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[N:16][C:17]=3[O:19][CH2:20][CH3:21])[NH:12][C:11]([CH3:22])=[C:10]2[C:23](O)=[O:24])=[C:5]([O:26][C:27]([F:30])([F:29])[F:28])[CH:4]=1)#[N:2].C(OCC)(=O)C.C(N1C=CN=C1)([N:39]1C=CN=C1)=O.N>CN(C=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[N:16][C:17]=3[O:19][CH2:20][CH3:21])[NH:12][C:11]([CH3:22])=[C:10]2[C:23]([NH2:39])=[O:24])=[C:5]([O:26][C:27]([F:28])([F:30])[F:29])[CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 682631,1'-CarbonyldiimidazoleHCID 59349639HCID 59349639, compound

Product 1

HCID 59349661HCID 59349661, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

200 mg (0.477 mmol) of the compound from Example 37A are introduced into 5 ml of ethyl acetate and, after addition of 96.7 mg (0.596 mmol) of 1,1′-carbonyldiimidazole, stirred at room temperature overnight (TLC check: insufficient reaction). Then 1 ml of DMF is added, and the mixture is stirred at room temperature for a further night (TLC check: complete conversion). The volatile components are removed in a rotary evaporator, and the residue is taken up in 4 ml of DMF. Then 663 μl of ammonia (28% by weight solution in water, 4.77 mmol) are added, and the reaction mixture is heated at 100° C. in a closed vessel overnight. After cooling, 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). 140 mg (70% of theory) of the title compound are obtained.

Workup

  1. custom(TLC check: insufficient reaction)
  2. stirringthe mixture is stirred at room temperature for a further night (TLC check: complete conversion)
  3. customThe volatile components are removed in a rotary evaporator
  4. temperaturethe reaction mixture is heated at 100° C. in a closed vessel overnight
  5. temperatureAfter cooling
  6. customthe solvent is removed under reduced pressure
  7. 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-3d49e0c751444842abff3c37a6a0371a
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

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