Hydrochloric Acid → HCID 21107389, compound

HRID 1765534Notes

Reaction equation

HRID 1765534 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].[CH:26]([NH2:29])([CH3:28])[CH3:27].CN1CCCC1=O.Cl>[Cl-].[Na+].O.ClCCl>[ClH:1].[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][C@@H:23]([OH:24])[CH2:25][NH:29][CH:26]([CH3:28])[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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6363IsopropylamineHCID 13387N-methyl-2-pyrrolidoneHCID 21107405HCID 21107405, compound

Product 1

HCID 21107389HCID 21107389, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-Chloro-5-[(2R)-2-oxiranylmethyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (Example 5c) (133 mg), isopropylamine (3 mL) and 1-methyl-2-pyrrolidinone (5 mL) were heated together at 80° C. in a sealed tube for 22 hours, cooled and poured into brine (50 mL), extracted into ethyl acetate (3×50 mL), washed with brine (3×50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to give an oil. This was purified by Waters' MCX resin and then by column chromatography eluting with 19:1:0.1 dichloromethane/methanol/ammonia. The oil obtained was dissolved in dichloromethane (5 mL) and 1M ethereal hydrogen chloride (4 mL) was added. The mixture was concentrated to give the titled compound as a solid (85 mg).

Workup

  1. temperaturecooled
  2. extractionextracted into ethyl acetate (3×50 mL)
  3. washwashed with brine (3×50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil
  8. customThis was purified by Waters' MCX resin
  9. washby column chromatography eluting with 19:1:0.1 dichloromethane/methanol/ammonia
  10. customThe oil obtained
  11. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-a24420ce378146e1b169bc4652bd4a8e
Source dataset
uspto-grants-2007_06
Patent number
US07227038B2

Reaction notes

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