Water → HCID 67427681, compound

HRID 2362765Notes

Reaction equation

HRID 2362765 reaction equation
[CH:1]1([N:6]=[C:7]=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[ClH:16].Cl.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32]([C@@H:34]3[CH:39]4[CH2:40][CH2:41][N:36]([CH2:37][CH2:38]4)[CH2:35]3)=[O:33])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1.O>CN(C=O)C>[ClH:16].[CH:1]1([NH:6][C:7]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:26]=[CH:27][C:28]([NH:31][C:32]([C@@H:34]4[CH:39]5[CH2:38][CH2:37][N:36]([CH2:41][CH2:40]5)[CH2:35]4)=[O:33])=[CH:29][CH:30]=3)=[CH:21][CH:20]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 643500Cyclopentyl IsocyanateHCID 67427707(3R)-N-(4'-Aminobiphenyl-4-yl)quinuclidine-3-carboxamide dihydrochloride

Product 1

HCID 67427681HCID 67427681, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

33.8 mg (0.30 mmol) of cyclopentyl isocyanate and 84.8 μl (0.61 mmol) of triethylamine are added to a solution of 60 mg (0.15 mmol) of ((3R)—N-(4′-aminobiphenyl-4-yl)quinuclidine-3-carboxamide dihydrochloride (Example 7A) in 0.5 ml of DMF. After 18 h at room temperature, 5 ml of water are added to the reaction mixture. The resulting precipitate is filtered off with suction, washed with water and dried under high vacuum. A preparative HPLC is carried out for further purification. The product fractions are concentrated, mixed with 3 ml of 1 N hydrochloric acid, again concentrated and dried under high vacuum. 28 mg (39.2% of theory) of the title compound are obtained.

Workup

  1. filtrationThe resulting precipitate is filtered off with suction
  2. washwashed with water
  3. customdried under high vacuum
  4. customA preparative HPLC is carried out for further purification
  5. concentrationThe product fractions are concentrated
  6. additionmixed with 3 ml of 1 N hydrochloric acid
  7. concentrationagain concentrated
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-0ca3c73318384f0aa71d4ac630da91df
Source dataset
uspto-grants-2014_04
Patent number
US08691840B2

Reaction notes

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