Benzoyl chloride → HCID 68431772, compound

HRID 658221Notes

Reaction equation

HRID 658221 reaction equation
Cl.Cl.[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[C@@H:5]([NH:11][C:12]([C:14]1[S:15][C:16]3[CH:22]=[C:21]([NH2:23])[CH:20]=[CH:19][C:17]=3[CH:18]=1)=[O:13])[CH2:4]2.C(N(CC)CC)C.[C:31]([Cl:39])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C>[ClH:39].[N:3]12[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10]1)[C@@H:5]([NH:11][C:12]([C:14]1[S:15][C:16]3[CH:22]=[C:21]([NH:23][C:31](=[O:38])[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:20]=[CH:19][C:17]=3[CH:18]=1)=[O:13])[CH2:4]2

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 66904443HCID 66904443, compound

Product 1

HCID 68431772HCID 68431772, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

40 mg (0.11 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-amino-1-benzothiophene-2-carboxamide dihydrochloride are dissolved in 2 ml of DMF, and 59.6 μl (0.43 mmol) of triethylamine are added. 30 mg (0.21 mmol) of benzoyl chloride are added. The reaction mixture is stirred at RT for 18 h and then separated by preparative HPLC. The product fraction is concentrated under reduced pressure, a mixture of acetonitrile and 1N hydrochloric acid is added, and the mixture is then again concentrated and dried under high vacuum. 32 mg (67.8% of theory) of the title compound are obtained.

Workup

  1. customseparated by preparative HPLC
  2. concentrationThe product fraction is concentrated under reduced pressure
  3. additiona mixture of acetonitrile and 1N hydrochloric acid
  4. additionis added
  5. concentrationthe mixture is then again concentrated
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-480b8702fdc9489f92a04b8f0d4c3884
Source dataset
uspto-grants-2011_12
Patent number
US08076355B2

Reaction notes

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