Piconol → Pyridin-2-ylmethyl{4-[({3-[(tert-butoxycarbonyl)amino]-6-phenylpyridin-2-yl}amino)carbonyl]benzyl}carbamate

HRID 1256673Notes

Reaction equation

HRID 1256673 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][OH:8].C1N=CN([C:14](N2C=NC=C2)=[O:15])C=1.[C:21]([O:25][C:26](=[O:51])[NH:27][C:28]1[C:29]([NH:40][C:41](=[O:50])[C:42]2[CH:47]=[CH:46][C:45]([CH2:48][NH2:49])=[CH:44][CH:43]=2)=[N:30][C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:32][CH:33]=1)([CH3:24])([CH3:23])[CH3:22].C1CCN2C(=NCCC2)CC1>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:14](=[O:15])[NH:49][CH2:48][C:45]1[CH:44]=[CH:43][C:42]([C:41]([NH:40][C:29]2[C:28]([NH:27][C:26]([O:25][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:51])=[CH:33][CH:32]=[C:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:30]=2)=[O:50])=[CH:47][CH:46]=1

Participants

6

Reactant 4

HCID 11474Piconol2×HCID 682631,1'-Carbonyldiimidazole2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57745571Tert-butyl(2-{[4-(aminomethyl)benzoyl]amino}-6-phenylpyridin-3-yl)carbamate

Product 1

HCID 59627872Pyridin-2-ylmethyl{4-[({3-[(tert-butoxycarbonyl)amino]-6-phenylpyridin-2-yl}amino)carbonyl]benzyl}carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pyridine-2-methanol (0.0345 ml, 0.358 mmol) was added to a 0° C. cooled mixture of CDI (58.0 mg, 0.358 mmol) in THF (5 mL) and the reaction was stirred at room temperature for 1 h. Tert-butyl(2-{[4-(aminomethyl)benzoyl]amino}-6-phenylpyridin-3-yl)carbamate (150 mg, 0.358 mmol) was added to the reaction with TEA (0.050 ml, 0.358 mmol) and DBU (0.054 ml, 0.358 mmol) and the reaction stirred for 2 hours. LC/MS indicated the presence of the addition of the free amine to the CDI and thus another equivalent of pyridine-2-methanol (0.345 ml, 0.358 mmol) was added and the reaction stirred overnight. LC/MS indicated the formation of the desired product. Following evaporation of THF, water was added and the organic product was extracted (3×) with EtOAc, washed with brine and dried over sodium sulfate. The residue was purified by column chromatography on silica gel Biotage 25S, eluting with EtOAc/hexanes (0%-100%). MS: cal'd 554 (MH+), exp 554 (MH+).

Workup

  1. temperaturecooled
  2. stirringthe reaction stirred for 2 hours
  3. stirringthe reaction stirred overnight

Sources & evidence

ORD record
ord-279a3c261c2b424ca2340591ffcf3f36
Source dataset
uspto-grants-2013_06
Patent number
US08461189B2

Reaction notes

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