Dichloromethane → 3-[8-Amino-1-(3-benzyloxy-phenyl)-imidazo[1,5-a]pyrazin-3-yl]cyclobutanecarbaldehyde

HRID 2373915Notes

Reaction equation

HRID 2373915 reaction equation
C(Cl)Cl.[CH2:4]([O:11][C:12]1[CH:13]=[C:14]([C:18]2[N:19]=[C:20]([CH:28]3[CH2:31][C:30](=[CH:32][O:33]C)[CH2:29]3)[N:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH2:27])[C:22]=23)[CH:15]=[CH:16][CH:17]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(C(O)=O)(F)(F)F.C([O-])([O-])=O.[K+].[K+]>O>[NH2:27][C:23]1[C:22]2[N:21]([C:20]([CH:28]3[CH2:31][CH:30]([CH:32]=[O:33])[CH2:29]3)=[N:19][C:18]=2[C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH2:4][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:13]=2)[CH:26]=[CH:25][N:24]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 111541581-(3-Benzyloxy-phenyl)-3-(3-methoxymethylene-cyclobutyl)-imidazo[1,5-a]pyrazin-8-ylamine

Product 1

HCID 112465273-[8-Amino-1-(3-benzyloxy-phenyl)-imidazo[1,5-a]pyrazin-3-yl]cyclobutanecarbaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a methylene chloride solution (6.0 mL) of 1-(3-Benzyloxy-phenyl)-3-(3-methoxymethylene-cyclobutyl)-imidazo[1,5-a]pyrazin-8-ylamine (287.0 mg, 0.696 mmol), CF3CO2H (0.11 mL, 1.392 mmol) was added, followed by H2O (0.5 mL). The reaction mixture was allowed to react for 1 h at rt. After which an ethanolic solution (5.0 mL) of K2CO3 (192.3 mg, 1.392 mmol) was added to the reaction and allowed to stir at rt for an additional 2 h. The reaction mixture extracted between water and EtOAc. The organic layers were washed with brine (1×), dried over Na2SO4, filtered and concentrated in vacuo to yield the desired product as a brown solid; 1H NMR (CDCl3, 400 MHz) (mixture of cis and trans isomers) δ 2.45-2.84 (m, 4H), 3.25-3.32 (m, 1H), 3.74-3.79 (m, 1H), 5.22 (s, 2H), 6.84-6.85 (m, 1H), 7.00-7.17 (m, 5H), 7.27-7.39 (m, 6H), 9.69 (s, 1H), 9.88 (s, 1H); MS (ES) 399.07 (M+1), 400.0 (M+2), 401.0 (M+3).

Workup

  1. customto react for 1 h at rt
  2. extractionThe reaction mixture extracted between water and EtOAc
  3. washThe organic layers were washed with brine (1×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04f63fbdf20f4bf1bf1794d6a8175865
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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