Hydrochloric Acid → HCID 21107395, compound

HRID 1765533Notes

Reaction equation

HRID 1765533 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][C@@H:23]2[CH2:25][O:24]2)=[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].[CH2:26]([NH2:28])[CH3:27].Cl>ClCCl>[ClH:1].[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][C@@H:23]([OH:24])[CH2:25][NH:28][CH2:26][CH3:27])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:15][CH:14]3[CH2:16][CH:10]([CH2:11][CH:12]([CH2:13]3)[CH2:17]1)[CH2:9]2)=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 21107405HCID 21107405, compound

Product 1

HCID 21107395HCID 21107395, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-5-[(2R)-2-oxiranylmethyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (Example 5c) (452mg), ethylamine (70% aqueous solution, 5 mL) and tetrahydrofuiran (15 mL) were heated together at 50° C. under nitrogen for 20 hours, cooled and concentrated to give an oil. This was purified by Waters' MCX resin (mixed-mode cation exchanger) and then by column chromatography eluting with 19:1:0.1 dichloromethane/methanol/ammonia. The oil obtained was dissolved in dichloromethane (5 mL) and one molar (1M) ethereal hydrogen chloride (4 mL) was added. The mixture was concentrated to give the sub-titled compound as a solid (415 mg).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customto give an oil
  4. customThis was purified by Waters' MCX resin (mixed-mode cation exchanger)
  5. washby column chromatography eluting with 19:1:0.1 dichloromethane/methanol/ammonia
  6. customThe oil obtained
  7. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-4c51ec026e724a45a75e323c098fa279
Source dataset
uspto-grants-2007_06
Patent number
US07227038B2

Reaction notes

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