Acetic Acid → HCID 85329688, compound

HRID 858152Notes

Reaction equation

HRID 858152 reaction equation
[C:1]([OH:4])(=O)C.[Cl:5][C:6]1[CH:7]=[C:8]([NH2:22])[CH:9]=[CH:10][C:11]=1[S:12][CH:13]1[CH2:19][CH:18]2[N:20]([CH3:21])[CH:15]([CH2:16][CH2:17]2)[CH2:14]1>C(O)=O>[Cl:5][C:6]1[CH:7]=[C:8]([NH:22][CH:1]=[O:4])[CH:9]=[CH:10][C:11]=1[S:12][CH:13]1[CH2:14][CH:15]2[N:20]([CH3:21])[CH:18]([CH2:17][CH2:16]2)[CH2:19]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 69524649HCID 69524649, compound

Product 1

HCID 85329688HCID 85329688, compoundYield 13.7%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of acetic acid (0.96 g) and formic acid (0.53 g) was heated under reflux for 2 hours. To this was added 3-chloro-4-[(8-methyl-8-azabicylo[3.2.1]oct-3-yl)thio]phenylamine (265 mg) and heating continued for 1.5 hours. The crude mixture was placed on an SCX cartridge and eluted with methanol followed by 2M ammonia in methanol. The impure product was then subjected to flash chroamtography on silica gel (gradient elution with increasing percentage of methanol in chloroform) to yield material of 93% purity. Final clean up by preparative LC-MS gave 3-chloro-4-[(8-methyl-8-azabicylo[3.2.1]oct-3-yl)thio]phenylformamide (40 mg)

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureheating
  4. washeluted with methanol
  5. customto yield material of 93% purity

Sources & evidence

ORD record
ord-7c9efe8497b1460c99e45e68250d7f78
Source dataset
uspto-grants-2006_12
Patent number
US07148236B2

Reaction notes

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