HCID 178491807, compound → HCID 178491806, compound

HRID 1435226Notes

Reaction equation

HRID 1435226 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]2[N:20]=[C:19]([NH2:21])[C:18]([C:22](=[O:32])[C:23]3[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=3[O:30][CH3:31])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[NH2:21][C:19]1[C:18]([C:22]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[O:30][CH3:31])=[O:32])=[CH:17][N:16]=[C:15]([NH:14][C@H:11]2[CH2:12][CH2:13][C@H:8]([NH2:7])[CH2:9][CH2:10]2)[N:20]=1

Participants

3

Reactant 1

HCID 178491807HCID 178491807, compound

Product 1

HCID 178491806HCID 178491806, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Trans-[4-[4-amino-5-(5-fluoro-2-methoxy-benzoyl)-pyrimidin-2-ylamino]-cyclohexyl]-carbamic acid tert-butyl ester (1.32 g) obtained from Example 113 was dissolved in 50% trifluoroacetic acid/dichloromethane (30 mL) and the solution was stirred at room temperature for 30 minutes. The solvent was removed and the residue was treated with saturated aqueous sodium bicarbonate solution. The mixture was extracted three times with ethyl acetate/tetrahydrofuran (3:1, 30 mL). The extracts were combined, dried (Na2SO4) and concentrated under reduced pressure to a solid (980 mg). Yield, 95%. MS(ES) (M+H)+=360.

Workup

  1. customThe solvent was removed
  2. additionthe residue was treated with saturated aqueous sodium bicarbonate solution
  3. extractionThe mixture was extracted three times with ethyl acetate/tetrahydrofuran (3:1, 30 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure to a solid (980 mg)
  6. customYield

Sources & evidence

ORD record
ord-ab9a9aa2c4ba44179ebd20f14ee142e5
Source dataset
uspto-grants-2009_11
Patent number
US07615634B2

Reaction notes

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