Trifluoroacetic acid → HCID 24811285, compound

HRID 1693271Notes

Reaction equation

HRID 1693271 reaction equation
FC(F)(F)C(O)=O.[C:8]([CH:10]1[CH2:20][C:19]2[C:21]3[C:16]([N:17]([CH2:22][C:23]4[C:28]([CH3:29])=[C:27]([O:30][CH3:31])[C:26]([CH3:32])=[CH:25][N:24]=4)[N:18]=2)=[N:15][C:14]([N:33](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[N:13][C:12]=3[S:11]1)#[N:9].CC1C=CC(S(OC(C#N)CC2C3C(=NC(N(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=NC=3Cl)N(CC3C(C)=C(OC)C(C)=CN=3)N=2)(=O)=O)=CC=1>ClCCl>[NH2:33][C:14]1[N:15]=[C:16]2[C:21]3[C:19]([CH2:20][CH:10]([C:8]#[N:9])[S:11][C:12]=3[N:13]=1)=[N:18][N:17]2[CH2:22][C:23]1[C:28]([CH3:29])=[C:27]([O:30][CH3:31])[C:26]([CH3:32])=[CH:25][N:24]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 44476495HCID 44476495, compoundHCID 59311568HCID 59311568, compound

Product 1

HCID 24811285HCID 24811285, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.25 mL) was added to a mixture composed of di-tert-butyl {7-cyano-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-7,8-dihydro-2H-6-thia-1,2,3,5-tetraazaacenaphthylen-4-yl}imidodicarbonate of Step 4) of Example 3 (30 mg) and dichloromethane (1 mL). Then, the ice bath was removed and the mixture was stirred for one hour. After confirming that the raw material disappeared, the reaction mixture was concentrated under reduced pressure. A saturated sodium bicarbonate solution was added to the resulting residue. The precipitated solid was collected by filtration and washed with water. The resulting solid was dried to obtain the title compound (13.8 mg, 71%).

Workup

  1. customThen, the ice bath was removed
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionA saturated sodium bicarbonate solution was added to the resulting residue
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customThe resulting solid was dried

Sources & evidence

ORD record
ord-3e1e94a8d6f649109266134b38bb6959
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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