Hydrochloric Acid → HCID 21107391, compound

HRID 1765535Notes

Reaction equation

HRID 1765535 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].[NH2:26][CH2:27][CH2:28][CH2:29][OH:30].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:26][CH2:27][CH2:28][CH2:29][OH:30])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:9][CH:10]3[CH2:16][CH:14]([CH2:13][CH:12]([CH2:11]3)[CH2:17]1)[CH2:15]2)=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 90863-Amino-1-propanolHCID 13387N-methyl-2-pyrrolidoneHCID 21107405HCID 21107405, compound

Product 1

HCID 21107391HCID 21107391, 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), 3-amino-1-propanol (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 9:1:0.1 dichloromethane/methanol/ammonia. This was further purified by reverse phase HPLC (gradient 25–95% acetonitrile in 0.2% aqueous trifluoroacetic acid on Xterra™ column). 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 (60 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 9:1:0.1 dichloromethane/methanol/ammonia
  10. customThis was further purified by reverse phase HPLC (gradient 25–95% acetonitrile in 0.2% aqueous trifluoroacetic acid on Xterra™ column)
  11. customThe oil obtained
  12. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-98b2af3cce0e477f96f3137973a8460d
Source dataset
uspto-grants-2007_06
Patent number
US07227038B2

Reaction notes

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