Ammonia → HCID 59349637, compound

HRID 2090225Notes

Reaction equation

HRID 2090225 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]([C:22]([F:25])([F:24])[F:23])=[C:10]2[C:26](O)=[O:27])=[C:5]([O:29][CH3:30])[CH:4]=1)#[N:2].C(N1C=CN=C1)([N:33]1C=CN=C1)=O.N>C(OCC)(=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]([C:22]([F:23])([F:24])[F:25])=[C:10]2[C:26]([NH2:33])=[O:27])=[C:5]([O:29][CH3:30])[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 59349642HCID 59349642, compound

Product 1

HCID 59349637HCID 59349637, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

180 mg (0.429 mmol) of the compound from Example 38A are introduced into 5 ml of ethyl acetate and, after addition of 87.0 mg (0.537 mmol) of 1,1′-carbonyldiimidazole, stirred at room temperature for two hours. Complete conversion is established by a TLC check. The volatile components are removed in a rotary evaporator, and the residue is taken up in 4 ml of DMF. Then 597 μl of ammonia (28% by weight solution in water, 4.29 mmol) are added, and the reaction mixture is heated at 100° C. in a closed vessel for three hours. 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). 10 mg (5% 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. in a closed vessel for three hours
  3. temperatureAfter cooling
  4. customthe solvent is removed under reduced pressure
  5. 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-daae3a458ce24465bcd03e64a9579e90
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

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