HCID 16753948, compound → HCID 178452621, compound

HRID 2373515Notes

Reaction equation

HRID 2373515 reaction equation
C[O:2][C:3]([C:5]1[C:10]([O:11]C(=O)C2C=CC=CC=2)=[C:9]([OH:20])[N:8]=[C:7]([C:21]2([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[N:6]=1)=O.[F:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][NH2:41])=[C:38]([S:44]([CH3:47])(=[O:46])=[O:45])[CH:37]=1>CO>[C:31]([O:30][C:28](=[O:29])[NH:27][C:21]1([C:7]2[N:6]=[C:5]([C:3]([NH:41][CH2:40][C:39]3[CH:42]=[CH:43][C:36]([F:35])=[CH:37][C:38]=3[S:44]([CH3:47])(=[O:46])=[O:45])=[O:2])[C:10]([OH:11])=[C:9]([OH:20])[N:8]=2)[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1)([CH3:33])([CH3:32])[CH3:34]

Participants

4

Reactant 2

HCID 16753948HCID 16753948, compoundHCID 178499079HCID 178499079, compound

Product 1

HCID 178452621HCID 178452621, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl-5-(benzoyloxy)-2-{4-[(tert-butoxycarbonyl)amino]tetrahydro-2H-pyran-4-yl}-6-hydroxypyrimidine-4-carboxylate (C-30) in dry MeOH was treated with 4-fluoro-2-(methylsulfonyl)benzylamine (2.5 eq.) at reflux for 2 hours. Solvent was removed in vacuo and the residue was taken up in ethyl acetate, washed with HCl 1N, brine, dried over Na2SO4. The filtrate was concentrated in vacuo and triturated with ethyl ether to obtain the crude title compound (C-31).

Workup

  1. temperatureat reflux for 2 hours
  2. customSolvent was removed in vacuo
  3. washwashed with HCl 1N, brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe filtrate was concentrated in vacuo
  6. customtriturated with ethyl ether

Sources & evidence

ORD record
ord-c719f7bef6ec4feb9bcb73a4374a9ed9
Source dataset
uspto-grants-2008_12
Patent number
US07459452B2

Reaction notes

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