4-Fluorobenzylamine → HCID 448749, compound

HRID 2219055Notes

Reaction equation

HRID 2219055 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[OH:10][C:11]1[C:30](=[O:31])[N:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]([NH:21][C@@H:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH3:23])[C:14]2=[N:13][C:12]=1[C:32](OC)=[O:33]>CO>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:32]([C:12]2[N:13]=[C:14]3[CH:20]([NH:21][C@@H:22]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH3:23])[CH2:19][CH2:18][CH2:17][CH2:16][N:15]3[C:30](=[O:31])[C:11]=2[OH:10])=[O:33])=[CH:4][CH:3]=1.[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH3+:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 673264-FluorobenzylamineHCID 67148233HCID 67148233, compound

Product 2

HCID 448749HCID 448749, compoundHCID 67148197HCID 67148197, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

p-Fluorobenzylamine (3 eq.) was added to the methyl 3-hydroxy-4-oxo-10-{[(1R)-1-phenylethyl]amino}-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepine-2-carboxylate (prepared as described in Step 5 or Step 5A) dissolved in methanol. The mixture was stirred at 70° C. overnight, then cooled to room temperature for use directly in Step 7. In an alternative procedure (Step 6A), the solvent was removed and the crude product crystallized from acetonitrile several times to obtain a single diasteroisomer of the title compound as the 4-fluorobenzylammonium salt with d.e.>95%

Workup

  1. temperaturecooled to room temperature for use directly in Step 7
  2. customIn an alternative procedure (Step 6A), the solvent was removed
  3. customthe crude product crystallized from acetonitrile several times

Sources & evidence

ORD record
ord-46dda1c810c44ed189e84de56743609f
Source dataset
uspto-grants-2008_08
Patent number
US07414045B2

Reaction notes

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