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

HRID 1012789Notes

Reaction equation

HRID 1012789 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.O>C1COCC1.CN(C=O)C>[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 962WaterHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 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 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), 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. 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-140d5daf2a5141b3ad8e9f5f04ddfe3a
Source dataset
uspto-grants-2011_07
Patent number
US07977485B2

Reaction notes

Loading…