Formic Acid → Tert-butyl(2-{[4-(aminomethyl)benzoyl]amino}-6-phenylpyridin-3-yl)carbamate

HRID 1256670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256670
N1C=CC=C(COC(=O)[NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([NH:20][C:21]3[C:26]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:25][CH:24]=[C:23]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[N:22]=3)=[O:19])=[CH:14][CH:13]=2)C=1.C(O)=O>CCO.[Pd]>[C:31]([O:30][C:28](=[O:29])[NH:27][C:26]1[C:21]([NH:20][C:18](=[O:19])[C:15]2[CH:14]=[CH:13][C:12]([CH2:11][NH2:10])=[CH:17][CH:16]=2)=[N:22][C:23]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:24][CH:25]=1)([CH3:34])([CH3:32])[CH3:33]

Komponenten

5

Edukt 2

HCID 284Formic AcidHCID 59627858Pyridin-3-ylmethyl{4-[({3-[(tert-butoxycarbonyl)amino]-6-phenylpyridin-2-yl}amino)carbonyl]benzyl}carbamate

Produkt 1

HCID 57745571Tert-butyl(2-{[4-(aminomethyl)benzoyl]amino}-6-phenylpyridin-3-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

pyridin-3-ylmethyl{4-[({3-[(tert-butoxycarbonyl)amino]-6-phenylpyridin-2-yl}amino)carbonyl]benzyl}carbamate (1.5 g, 2.71 mmol) was taken up in EtOH (10.84 mL) at 0° C., evacuated and backfilled with N2. Pd/C (0.288 g, 0.27 mmol) was added and the reaction was again purged and backfilled with N2. Formic acid (2 mL, 53 mmol) was added and the reaction was stirred at RT and monitored by LC/MS. Reaction was complete in 2 h. The reaction was filtered through Celite and evaporated. The residue was taken up in DCM and washed with satd NaHCO3 solution (2×50 mL). The combined organic fractions were dried over Na2SO4, filtered and evaporated in vacuo to provide tert-butyl(2-{[4-(aminomethyl)benzoyl]amino}-6-phenylpyridin-3-yl)carbamate. MS: cal'd 419 (MH+), exp 419 (MH+).

Aufarbeitung

  1. customevacuated
  2. customthe reaction was again purged
  3. customReaction
  4. filtrationThe reaction was filtered through Celite
  5. customevaporated
  6. washwashed with satd NaHCO3 solution (2×50 mL)
  7. dry with materialThe combined organic fractions were dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-59e59c3f47764de08556b42d20857853
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461189B2

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