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

HRID 1256670ノート

反応式

HRID 1256670 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-59e59c3f47764de08556b42d20857853
出典データセット
uspto-grants-2013_06
特許番号
US08461189B2

反応ノート

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