Acetyl chloride → HCID 67314319, compound

HRID 1012785Notes

Reaction equation

HRID 1012785 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.[C:28]([Cl:31])(=[O:30])[CH3:29].C(N(CC)CC)C>C1COCC1>[ClH:31].[C:28]([NH: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[CH2:24][CH2:23][N:22]([CH2:27][CH2:26]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)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 58675161HCID 58675161, compound

Product 1

HCID 67314319HCID 67314319, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

75 mg (0.16 mmol) of 7-(3-aminophenyl)-N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-1-benzofuran-2-carboxamide (Example 114), 18 μl (0.24 mmol) of acetyl chloride and 68 μl (0.49 mmol) of triethylamine are stirred in 2 ml of THF 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. Removal of the solvent under reduced pressure and drying under high vacuum results in 51 mg (72% 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-36b4c22875dc40b1a5d1ab350f81a714
Source dataset
uspto-grants-2011_07
Patent number
US07977485B2

Reaction notes

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