Methanesulfonyl chloride → HCID 11464734, compound

HRID 2362758Notes

Reaction equation

HRID 2362758 reaction equation
[CH3:1][S:2]([Cl:5])(=[O:4])=[O:3].Cl.Cl.[NH2:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C@@H:24]3[CH:29]4[CH2:30][CH2:31][N:26]([CH2:27][CH2:28]4)[CH2:25]3)=[O:23])=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1>CN(C=O)C.C(#N)C.O>[ClH:5].[CH3:1][S:2]([NH:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:22]([C@@H:24]3[CH:29]4[CH2:28][CH2:27][N:26]([CH2:31][CH2:30]4)[CH2:25]3)=[O:23])=[CH:19][CH:20]=2)[CH:12]=[CH:13][CH:14]=1)(=[O:4])=[O:3]

Participants

6

Reactant 2

HCID 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 triethylanaine 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. HPLC (Method 1): Rt=3.70 min. LC-MS (Method 2): Rt=2.45 min.; m/z=400 (M+H)+.

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-3d713b4501f84f6e845fc455d2eb101f
Source dataset
uspto-grants-2014_04
Patent number
US08691840B2

Reaction notes

Loading…