Hydrochloride methanol → HCID 11812863, compound

HRID 355508Notes

Reaction equation

HRID 355508 reaction equation
[NH2:1][C:2]1[N:6]([C@@H:7]2[O:20][C@H:19]([CH2:21][O:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@@H:9]([O:10][C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C@@H:8]2[F:31])[CH:5]=[N:4][C:3]=1[C:32](=[O:37])[CH2:33][N:34]=[N+]=[N-].Cl.CO.[H][H]>CO.[Pd]>[NH2:1][C:2]1[N:6]([C@@H:7]2[O:20][C@H:19]([CH2:21][O:22][C:23](=[O:30])[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C@@H:9]([O:10][C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C@@H:8]2[F:31])[CH:5]=[N:4][C:3]=1[C:32](=[O:37])[CH2:33][NH2:34]

Participants

6

Reactant 3

HCID 21893726Hydrochloride methanolHCID 54340169HCID 54340169, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11812863HCID 11812863, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound (17) obtained in step (8) above (567 mg) was dissolved in methanol (23 ml), to which was then added a 2.2M hydrogen chloride-methanol solution (0.75 ml). The resulting solution was subjected to a catalytic reduction by blowing hydrogen into the solution at room temperature in the presence as catalyst of palladium black for 1 hour (for the reduction of the azido group). The reaction solution so obtained was filtered and the filtrate was concentrated to leave a solid, which was then washed with diethyl ether, to afford the titled compound (18) as a solid (508 mg) which was insoluble in ethyl ether.

Workup

  1. customat room temperature
  2. customfor 1 hour
  3. customThe reaction solution so obtained
  4. filtrationwas filtered
  5. concentrationthe filtrate was concentrated
  6. customto leave a solid, which
  7. washwas then washed with diethyl ether

Sources & evidence

ORD record
ord-c63986b616a24b088b58f17d3c9e0d2f
Source dataset
uspto-grants-1998_11
Patent number
US05831072

Reaction notes

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