Dichloromethane → HCID 178469877, compound

HRID 57798Notes

Reaction equation

HRID 57798 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]2[N:13]=[C:14]([C:16]([OH:18])=O)[CH:15]=[C:9]2[NH:8][CH:7]=1)=[O:5])[CH3:2].C([N:21]([CH2:24][CH3:25])CC)C.[CH:26]1[CH:27]=[CH:28][C:29]2N(O)N=N[C:30]=2[CH:31]=1.CCN=C=NCCCN(C)C.[Cl:47]CCl>CO.O>[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]2[N:13]=[C:14]([C:16](=[O:18])[NH:21][CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([Cl:47])=[CH:28][CH:27]=3)[CH:15]=[C:9]2[NH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 178469878HCID 178469878, compound2×

Product 1

HCID 178469877HCID 178469877, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidine-2,6-dicarboxylic acid 6-ethyl ester (Key intermediate V) (176 mg, 0.7 mmol, 1 eq) in dichloromethane (5 mL) were added triethylamine (195 μL, 1.4 mmol, 2 eq), HOBT (142 mg, 1.05 mmol, 1.5 eq), the appropriate amine (0.8 mmol, 1.1 eq) and EDCI (201 mg, 1.05 mmol, 1.5 eq). The mixture was stirred at room temperature during 20 h. Water (10 mL) was then added and the aqueous phase was extracted with dichloromethane (2×15 mL). The organic layers were dried over magnesium sulfate, filtered and evaporated in vacuo. The crude residue was purified by flash chromatography using dichloromethane and methanol (100/0) to (80/20). The compound obtained was taken up in methanol and filtered to afford the expected compound as white powder (145 mg, 49% yield).

Workup

  1. extractionthe aqueous phase was extracted with dichloromethane (2×15 mL)
  2. dry with materialThe organic layers were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe crude residue was purified by flash chromatography
  6. customThe compound obtained
  7. filtrationfiltered

Sources & evidence

ORD record
ord-07e34588b7e143b1bc61109b06a78887
Source dataset
uspto-grants-2016_09
Patent number
US09434745B2

Reaction notes

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