Water → HCID 67314394, compound

HRID 1012788Notes

Reaction equation

HRID 1012788 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[O:15][C:14]([C:17]([NH:19][C@@H:20]4[CH:25]5[CH2:26][CH2:27][N:22]([CH2:23][CH2:24]5)[CH2:21]4)=[O:18])=[CH:13][C:12]=3[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH:28]1([C:32]([Cl:34])=[O:33])[CH2:31][CH2:30][CH2:29]1.C(N(CC)CC)C.O>C1COCC1>[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:4]4[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:32]([CH:28]5[CH2:31][CH2:30][CH2:29]5)=[O:33])[CH:3]=4)=[CH:9][CH:10]=[CH:11][C:12]=3[CH:13]=1)=[O:18])[CH2:21]2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 78705Cyclobutanecarbonyl chlorideHCID 58675161HCID 58675161, compound

Product 1

HCID 67314394HCID 67314394, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

75 mg (0.21 mmol) of 7-(3-aminophenyl)-N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-1-benzofuran-2-carboxamide (Example 114), 37 mg (0.31 mmol) of cyclobutanecarbonyl chloride and 87 μl (0.62 mmol) of triethylamine are stirred in 2 ml of THF at RT overnight. After addition of water, 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. Removal of the solvent under reduced pressure and drying under high vacuum result in 57 mg (57% 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. customRemoval of the solvent under reduced pressure
  6. customdrying under high vacuum

Sources & evidence

ORD record
ord-22cf456b7dfa4f79b2fb384fb514a2f9
Source dataset
uspto-grants-2011_07
Patent number
US07977485B2

Reaction notes

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