Hydrochloric Acid → HCID 21107397, compound

HRID 1765540Notes

Reaction equation

HRID 1765540 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].[CH3:26][NH2:27].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:27][CH3:26])=[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 6329MethylamineHCID 8028TetrahydrofuranHCID 21107406HCID 21107406, compound

Product 1

HCID 21107397HCID 21107397, 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), methylamine (40% 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 (121 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-49cfe74c237f4b09aecc7be288d3f449
Source dataset
uspto-grants-2007_06
Patent number
US07227038B2

Reaction notes

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