Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 18444815, compound

HRID 459950Notes

Reaction equation

HRID 459950 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[NH2:13].[CH2:14]([NH:16][C:17]1[C:22]([CH:23]=O)=[CH:21][N:20]=[C:19]([S:25][CH3:26])[N:18]=1)[CH3:15].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1(C)C=CC=CC=1>[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[N:13]=[CH:23][C:22]1[C:17]([NH:16][CH2:14][CH3:15])=[N:18][C:19]([S:25][CH3:26])=[N:20][CH:21]=1

Participants

5

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 102618922,6-Difluoro-3,5-dimethoxybenzenamineHCID 107504444-(Ethylamino)-2-(methylthio)pyrimidine-5-carbaldehyde

Product 1

HCID 18444815HCID 18444815, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

In a 500-mL round bottom flask, 3.00 g (15.86 mmol) of 2,6-difluoro-3,5-dimethoxy-phenylamine and 3.13 g (15.86 mmol) of 4-ethylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde in 150 mL of toluene with 1.11 g (4.76 mmol) of camphorsulfonic acid was fitted with a Dean Stark trap and heated at reflux. During the day, the toluene was drained 3 times from the finger, replenished with 100 mL of the solvent and continued heating at reflux under nitrogen atmosphere overnight. The toluene was concentrated in vacuo and dried to give 7.19 g (quantitative) of the title compound. No further purification was necessary. MS (APCI) (m+1)/z 369.1.

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. temperaturecontinued heating
  4. temperatureat reflux under nitrogen atmosphere overnight
  5. concentrationThe toluene was concentrated in vacuo
  6. customdried

Sources & evidence

ORD record
ord-02b9c45d8b1840fd81c7ef9f9f0a5932
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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