HCID 67242845, compound → HCID 67242788, compound

HRID 2422417Notes

Reaction equation

HRID 2422417 reaction equation
[ClH:1].[CH3:2][C:3]1[C:8]([N+:9]([O-])=O)=[C:7]([NH:12][C:13]2[CH:31]=[CH:30][C:16]([CH2:17][CH2:18][NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:15][CH:14]=2)[CH:6]=[C:5]([CH3:32])[N:4]=1>[Pt].CO>[ClH:1].[NH2:9][C:8]1[C:3]([CH3:2])=[N:4][C:5]([CH3:32])=[CH:6][C:7]=1[NH:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][CH2:18][NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:30][CH:31]=1

Participants

4

Reactant 1

HCID 67242845HCID 67242845, compound

Product 1

HCID 67242788HCID 67242788, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

To a clean, nitrogen-purged 1 L hydrogenation reactor were charged 5% Pt/C (625 mg), benzyl 4-(2,6-dimethyl-3-nitropyridin-4-ylamino)phenethylcarbamate hydrochloride (25.0 g, 54.7 mmoles) and methanol (550 mL). The reaction was stirred for at least 15 minutes and then purged sequentially with nitrogen and hydrogen. The reaction was then pressurized with hydrogen to between 18 and 25 psi at between 22° C. and 28° C. until HPLC showed no starting material remained. The reaction was purged with nitrogen and the catalyst was filtered on a water-wet celite-coated filter and the cake was washed with methanol (125 mL). The resulting solution of benzyl 4-(3-amino-2,6-dimethylpyridin-4-ylamino)phenethylcarbamate hydrochloride was transferred to a clean and dry nitrogen-purged 1 L round-bottom flask. Methanol was displaced atmospherically with 2-propanol to a final volume of approximately 125 mL. The reaction was then cooled to between 15° C. and 25° C. over at least 60 minutes and sampled for KF. The reaction was then filtered and washed with 2-propanol (75 mL). After blowing the cake with nitrogen for at least 15 minutes and drying under vacuum at 40° C. to 50° C. with nitrogen bleed for at least 12 hours, 21.0 g (49.2 mmoles) of benzyl 4-(3-amino-2,6-dimethylpyridin-4-ylamino)phenethylcarbamate hydrochloride was isolated in 89.9% yield.

Workup

  1. customTo a clean, nitrogen-purged 1 L hydrogenation reactor
  2. custompurged sequentially with nitrogen and hydrogen
  3. customwas then pressurized with hydrogen to between 18 and 25 psi at between 22° C. and 28° C. until HPLC
  4. customThe reaction was purged with nitrogen
  5. filtrationthe catalyst was filtered on a water-wet celite-coated filter
  6. washthe cake was washed with methanol (125 mL)
  7. custompurged 1 L round-bottom flask
  8. temperatureThe reaction was then cooled to between 15° C. and 25° C. over at least 60 minutes
  9. aliquotsampled for KF
  10. filtrationThe reaction was then filtered
  11. washwashed with 2-propanol (75 mL)
  12. customfor at least 15 minutes
  13. customdrying under vacuum at 40° C. to 50° C. with nitrogen
  14. waitbleed for at least 12 hours

Sources & evidence

ORD record
ord-bf426a1f255047119f06cefb3f9cd2ec
Source dataset
uspto-grants-2011_06
Patent number
US07960407B2

Reaction notes

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