Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 57677403, compound

HRID 492866Notes

Reaction equation

HRID 492866 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]=[C:12]=[S:13])=[O:10])=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[NH2:21][C:22]1[CH:46]=[CH:45][C:25]([O:26][C:27]2[CH:32]=[C:31]([NH:33][C:34]([N:36]3[CH2:40][CH2:39][C@@H:38]([CH2:41][N:42]([CH3:44])[CH3:43])[CH2:37]3)=[O:35])[N:30]=[CH:29][N:28]=2)=[C:24]([F:47])[CH:23]=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C(O)C>[CH3:44][N:42]([CH2:41][C@@H:38]1[CH2:39][CH2:40][N:36]([C:34]([NH:33][C:31]2[CH:32]=[C:27]([O:26][C:25]3[CH:45]=[CH:46][C:22]([NH:21][C:12]([NH:11][C:9](=[O:10])[CH2:8][C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[S:13])=[CH:23][C:24]=3[F:47])[N:28]=[CH:29][N:30]=2)=[O:35])[CH2:37]1)[CH3:43]

Participants

5

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 57677561HCID 57677561, compoundHCID 86602169HCID 86602169, compound

Product 1

HCID 57677403HCID 57677403, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After adding a 2-(4-fluorophenyl)acetyl isothiocyanate-toluene (0.2 M, 2.2 ml) solution to a solution of 4-(4-amino-2-fluorophenoxy)-6-{[(3S)-3-(dimethylaminomethyl)pyrrolidin-1-yl]carbonylamino}pyrimidine (105 mg) and (+)-10-camphorsulfonic acid (65 mg) in ethanol (2.5 ml) at room temperature, the mixture was stirred for 1 hour. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate and brine and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate:heptane=2:1, then ethyl acetate) to provide the title compound (60.5 mg, 38%) as white powder.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent

Sources & evidence

ORD record
ord-a0b21563d8c346caa3059e71f5052851
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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