Triethylamine → HCID 67313414, compound

HRID 1012783Notes

Reaction equation

HRID 1012783 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[O:15][C:14]([C:17]([NH:19][C@@H:20]3[CH:25]4[CH2:26][CH2:27][N:22]([CH2:23][CH2:24]4)[CH2:21]3)=[O:18])=[CH:13][C:12]=2[CH:11]=[CH:10][CH:9]=1.[CH:28]1([C:32]([Cl:34])=[O:33])[CH2:31][CH2:30][CH2:29]1.C(N(CC)CC)C>C1COCC1.CN(C=O)C>[ClH:34].[N:22]12[CH2:23][CH2:24][CH:25]([CH2:26][CH2:27]1)[C@@H:20]([NH:19][C:17]([C:14]1[O:15][C:16]3[C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[NH:1][C:32]([CH:28]4[CH2:31][CH2:30][CH2:29]4)=[O:33])=[CH:9][CH:10]=[CH:11][C:12]=3[CH:13]=1)=[O:18])[CH2:21]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78705Cyclobutanecarbonyl chlorideHCID 58485547HCID 58485547, compound

Product 1

HCID 67313414HCID 67313414, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

60 mg (0.15 mmol) of 7-(2-aminophenyl)-N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-1-benzofuran-2-carboxamide (Example 132), 26 mg (0.22 mmol) of cyclobutanecarbonyl chloride and 0.06 ml (0.44 mmol) of triethylamine are shaken in 2 ml of THF/DMF (1:1) at RT overnight. The solvent is removed under reduced pressure. Purification takes place by preparative HPLC. The product is dissolved in methanol, and an excess of 1N hydrochloric acid is added. The solvent is removed under reduced pressure. Drying under high vacuum results in 39 mg (56% of theory) of the title compound.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customPurification
  3. dissolutionThe product is dissolved in methanol
  4. additionan excess of 1N hydrochloric acid is added
  5. customThe solvent is removed under reduced pressure
  6. customDrying under high vacuum

Sources & evidence

ORD record
ord-84c70c8a03a34822a87f52985e3f8328
Source dataset
uspto-grants-2011_07
Patent number
US07977485B2

Reaction notes

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