Hydrochloric Acid → HCID 21900013, compound

HRID 1593825Notes

Reaction equation

HRID 1593825 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][O:23][CH2:24][CH2:25][OH:26])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36].Cl>ClCCl>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][O:23][CH2:24][CH2:25][O:26][S:35]([CH3:34])(=[O:37])=[O:36])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:15][CH:14]3[CH2:13][CH:12]([CH2:11][CH:10]([CH2:16]3)[CH2:9]1)[CH2:17]2)=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21900029HCID 21900029, compound

Product 1

HCID 21900013HCID 21900013, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-5-[(2-hydroxyethoxy)methyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.228 g, Example 25a) and triethylamine (0.21 ml) in dichloromethane (10 ml) were cooled to 5° C. under nitrogen and methanesulfonyl chloride (0.1 ml) was added. The mixture was stirred at room temperature for 20 h then poured into 2 N hydrochloric acid, and extracted into ethyl acetate. The combined extracts were washed with 2 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution then brine, and dried over magnesium sulfate. The organics were filtered and concentrated under reduced pressure to afford the subtitled compound as a white solid (0.160 g).

Workup

  1. extractionextracted into ethyl acetate
  2. washThe combined extracts were washed with 2 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution
  3. dry with materialbrine, and dried over magnesium sulfate
  4. filtrationThe organics were filtered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f3946fa380ba4a34a4d9416b2815ac2b
Source dataset
uspto-grants-2007_11
Patent number
US07297818B2

Reaction notes

Loading…