Dimethyl Sulfoxide → HCID 11464568, compound

HRID 2362769Notes

Reaction equation

HRID 2362769 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.[CH3:27][O:28][CH2:29][C:30]([Cl:32])=[O:31].CS(C)=O>N1C=CC=CC=1>[ClH:32].[CH3:27][O:28][CH2:29][C:30]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17]([C@@H:19]3[CH:24]4[CH2:23][CH2:22][N:21]([CH2:26][CH2:25]4)[CH2:20]3)=[O:18])=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)=[O:31]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 96623Methoxyacetyl chlorideHCID 67427707(3R)-N-(4'-Aminobiphenyl-4-yl)quinuclidine-3-carboxamide dihydrochloride

Product 1

HCID 11464568HCID 11464568, 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 27.5 mg (0.25 mmol) of methoxyacetyl 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. 16 mg (29.4% 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-a50f1528d4594648a558e0cb4d824d66
Source dataset
uspto-grants-2014_04
Patent number
US08691840B2

Reaction notes

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