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

HRID 1256670Notes

Reaction equation

HRID 1256670 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-59e59c3f47764de08556b42d20857853
Source dataset
uspto-grants-2013_06
Patent number
US08461189B2

Reaction notes

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