Hydrochloric Acid → HCID 69484895, compound

HRID 1765541Notes

Reaction equation

HRID 1765541 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].O1CCCC1.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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 8028TetrahydrofuranHCID 21107406HCID 21107406, compound

Product 1

HCID 69484895HCID 69484895, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-5-[(2S)-2-oxiranylmethyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (Example 13b) (110 mg), ethylamine (70% aqueous solution, 2 mL) and tetrahydrofuran (10 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 and then by column chromatography eluting with 9:1:0.1 dichloromethane/methanol/ammonia. The oil obtained was dissolved in dichloromethane (5 mL) and 1M ethereal hydrogen chloride (4 mL) was added. The resulting white solid was filtered off to give the titled compound (109 mg).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customto give an oil
  4. customThis was purified by Waters' MCX resin
  5. washby column chromatography eluting with 9:1:0.1 dichloromethane/methanol/ammonia
  6. customThe oil obtained
  7. filtrationThe resulting white solid was filtered off

Sources & evidence

ORD record
ord-f469189b615a4e45b26ec4e9fc79f71c
Source dataset
uspto-grants-2007_06
Patent number
US07227038B2

Reaction notes

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