Triethylamine → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-{2-[(cyclopropylcarbonyl)amino]phenyl}-1-benzofuran-2-carboxamide hydrochloride

HRID 2179663Notes

Reaction equation

HRID 2179663 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:31]([Cl:33])=[O:32])[CH2:30][CH2:29]1.C(N(CC)CC)C.C1COCC1.CN(C=O)C>O>[ClH:33].[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:31]([CH:28]4[CH2:30][CH2:29]4)=[O:32])=[CH:9][CH:10]=[CH:11][C:12]=3[CH:13]=1)=[O:18])[CH2:21]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 21974620tetrahydrofuran N,N-dimethylformamideHCID 58485547HCID 58485547, compound

Product 1

HCID 67314798N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-{2-[(cyclopropylcarbonyl)amino]phenyl}-1-benzofuran-2-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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), 20 μl (0.31 mmol) of cyclopropylcarbonyl chloride and 87 μl (0.62 mmol) of triethylamine are stirred in. 2 ml of THF/DMF (1:1) 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 27 mg (40% of theory) of the title compound.

Workup

  1. customat RT
  2. customovernight
  3. customthe solvent is removed under reduced pressure
  4. customPurification
  5. dissolutionThe product is dissolved in methanol
  6. additionan excess of 1N hydrochloric acid is added
  7. customRemoval of the solvent under reduced pressure
  8. customdrying under high vacuum

Sources & evidence

ORD record
ord-69c0dd4b50134ebba88bf05fba730d7a
Source dataset
uspto-grants-2015_06
Patent number
US09067931B2

Reaction notes

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