4-Fluorobenzylamine → HCID 448749, compound

HRID 2426268Notes

Reaction equation

HRID 2426268 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 diastereoisomer 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-db0f0a347e26408f89a81faed7481ae6
Source dataset
uspto-grants-2011_06
Patent number
US07968553B2

Reaction notes

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