Triethylamine → HCID 11464734, compound

HRID 899180Notes

Reaction equation

HRID 899180 reaction equation
C(N(CC)CC)C.[CH3:8][S:9]([Cl:12])(=[O:11])=[O:10].Cl.Cl.[NH2:15][C:16]1[CH:17]=[C:18]([C:22]2[CH:27]=[CH:26][C:25]([NH:28][C:29]([C@@H:31]3[CH:36]4[CH2:37][CH2:38][N:33]([CH2:34][CH2:35]4)[CH2:32]3)=[O:30])=[CH:24][CH:23]=2)[CH:19]=[CH:20][CH:21]=1>CN(C=O)C.C(#N)C.O>[ClH:12].[CH3:8][S:9]([NH:15][C:16]1[CH:17]=[C:18]([C:22]2[CH:23]=[CH:24][C:25]([NH:28][C:29]([C@@H:31]3[CH:36]4[CH2:35][CH2:34][N:33]([CH2:38][CH2:37]4)[CH2:32]3)=[O:30])=[CH:26][CH:27]=2)[CH:19]=[CH:20][CH:21]=1)(=[O:11])=[O:10]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67428989HCID 67428989, compound

Product 1

HCID 11464734HCID 11464734, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

63.6 μl (0.46 mmol) of triethylamine and 21.2 μl (0.27 mmol) of methanesulfonyl chloride are added to a solution of 60 mg (0.09 mmol) of (3R)-N-(3′-aminobiphenyl-4-yl)quinuclidine-3-carboxamide dihydrochloride (Example 8A) in 1 ml of DMF at room temperature. After 18 h at room temperature, the reaction mixture is diluted with a 1:1 mixture of acetonitrile and water and purified by preparative HPLC. The product fractions are concentrated, taken up in 1 ml of 1 N hydrochloric acid, again concentrated and dried under high vacuum. 14 mg (35.2% of theory) of the title compound are obtained.

Workup

  1. custompurified by preparative HPLC
  2. concentrationThe product fractions are concentrated
  3. concentrationagain concentrated
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-74e5cda541b740e394934a582511bedf
Source dataset
uspto-grants-2008_04
Patent number
US07354930B2

Reaction notes

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