Water → HCID 67314395, compound

HRID 1012787Notes

Reaction equation

HRID 1012787 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.[CH3:28][O:29][CH2:30][C:31]([Cl:33])=[O:32].C(N(CC)CC)C.O>C1COCC1>[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:4]4[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:31](=[O:32])[CH2:30][O:29][CH3:28])[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 96623Methoxyacetyl chlorideHCID 58675161HCID 58675161, compound

Product 1

HCID 67314395HCID 67314395, 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), 21 μl (0.31 mmol) of methoxyacetyl 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 56 mg (55% 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-c8f1dbb448414201ab013659abcacfad
Source dataset
uspto-grants-2011_07
Patent number
US07977485B2

Reaction notes

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