Hydrochloric Acid → HCID 21900013, compound

HRID 719643Notes

Reaction equation

HRID 719643 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 2N hydrochloric acid, and extracted into ethyl acetate. The combined extracts were washed with 2N 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 2N 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-a6b64c053f2b4d1ba1eed91b452c5a20
Source dataset
uspto-grants-2006_11
Patent number
US07132457B2

Reaction notes

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