Dimethyl Sulfoxide → HCID 11178523, compound

HRID 588355Notes

Reaction equation

HRID 588355 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([C@@H:19]3[CH:24]4[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]4)[CH2:20]3)=[O:18])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[CH:27]1([C:32]([Cl:34])=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28]1.CS(C)=O>N1C=CC=CC=1>[ClH:34].[CH:27]1([C:32]([NH:3][C:4]2[CH:9]=[CH:8][C:7]([C:10]3[CH:11]=[CH:12][C:13]([NH:16][C:17]([C@@H:19]4[CH:24]5[CH2:23][CH2:22][N:21]([CH2:26][CH2:25]5)[CH2:20]4)=[O:18])=[CH:14][CH:15]=3)=[CH:6][CH:5]=2)=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 78284Cyclopentanecarbonyl chlorideHCID 67427707(3R)-N-(4'-Aminobiphenyl-4-yl)quinuclidine-3-carboxamide dihydrochloride

Product 1

HCID 11178523HCID 11178523, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 50 mg (0.13 mmol) of ((3R)—N-(4′-aminobiphenyl-4-yl)quinuclidine-3-carboxamide dihydrochloride (Example 7A) and 38.5 μl (0.32 mmol) of cyclopentanecarbonyl chloride in 1.0 ml of pyridine is stirred at room temperature for 18 h. The reaction mixture is mixed with 3 ml of DMSO and purified by preparative HPLC. The product fractions are concentrated, mixed with 5 ml of 1 N hydrochloric acid, again concentrated and dried under high vacuum. 22 mg (38.2% of theory) of the title compound are obtained.

Workup

  1. custompurified by preparative HPLC
  2. concentrationThe product fractions are concentrated
  3. additionmixed with 5 ml of 1 N hydrochloric acid
  4. concentrationagain concentrated
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-240bca3499d044d0b60ba65f7a45b989
Source dataset
uspto-grants-2016_01
Patent number
US09227964B2

Reaction notes

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