Dibutylamine → HCID 71062377, compound

HRID 529037Notes

Reaction equation

HRID 529037 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][C:9]=2[C:18]([N:20]2[CH2:29][CH2:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:21]2)=[O:19])[CH:5]=[CH:4][N:3]=1.[CH2:30]([NH:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:31][CH2:32][CH3:33].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:30]([N:34]([CH2:35][CH2:36][CH2:37][CH3:38])[C:2]1[N:7]=[C:6]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=2[C:18]([N:20]2[CH2:29][CH2:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:21]2)=[O:19])[CH:5]=[CH:4][N:3]=1)[CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 8148DibutylamineHCID 11430Potassium CarbonateHCID 86718951HCID 86718951, compound

Product 1

HCID 71062377HCID 71062377, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 4-(2-chloropyrimidin-4-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (82 mg, 0.20 mmol) in DMF (1.0 mL) were added dibutylamine (Aldrich, 52 mg, 0.40 mmol) and potassium carbonate (83 mg, 0.60 mmol). The reaction mixture was heated at 60° C. for 5 h and 80° C. for 3 h. After cooling to room temperature, the reaction mixture was quenched with cold water. The mixture was extracted with EtOAc (3×). The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give the title compound (69 mg, 95%). MS (ESI+) m/z 501.2 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was quenched with cold water
  3. extractionThe mixture was extracted with EtOAc (3×)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d31c7eca452043faa67681b09aa78ac9
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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