4-Fluorobenzylamine → HCID 54677624, compound

HRID 1375574Notes

Reaction equation

HRID 1375574 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[C:7]([C@@H:22]2[CH2:26][C:25]([F:28])([F:27])[CH2:24][N:23]2[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[N:8]([CH3:21])[C:9](=[O:20])[C:10]=1[O:11]C(=O)C1C=CC=CC=1)=O.[F:39][C:40]1[CH:47]=[CH:46][C:43]([CH2:44][NH2:45])=[CH:42][CH:41]=1>CO>[CH2:32]([O:31][C:29]([N:23]1[CH2:24][C:25]([F:28])([F:27])[CH2:26][C@H:22]1[C:7]1[N:8]([CH3:21])[C:9](=[O:20])[C:10]([OH:11])=[C:5]([C:3]([NH:45][CH2:44][C:43]2[CH:46]=[CH:47][C:40]([F:39])=[CH:41][CH:42]=2)=[O:2])[N:6]=1)=[O:30])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 673264-FluorobenzylamineHCID 23626788HCID 23626788, compound

Product 1

HCID 54677624HCID 54677624, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl-5-(benzoyloxy)-2-{(2S)-1-[(benzyloxy)carbonyl]-4,4-difluoropyrrolidin-2-yl}-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylate in dry MeOH was treated with 4-fluorobenzyl amine (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 title compound as a 1.5:1 mixture of two rotamers by NMR.

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-1dcb688ec5074f639f65ed4a83120fd2
Source dataset
uspto-grants-2007_01
Patent number
US07169780B2

Reaction notes

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