Triethylamine → 1-{1-[6-(4-Nitro-2,3-dihydroindole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydroimidazo[4,5-b]pyridin-2-one

HRID 74529Notes

Reaction equation

HRID 74529 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[O:23]=[C:24]1[NH:32][C:27]2=[N:28][CH:29]=[CH:30][CH:31]=[C:26]2[N:25]1[CH:33]1[CH2:38][CH2:37][N:36]([C:39]2[N:44]=[CH:43][N:42]=[C:41]([C:45](O)=[O:46])[CH:40]=2)[CH2:35][CH2:34]1.[N+:48]([C:51]1[CH:59]=[CH:58][CH:57]=[C:56]2[C:52]=1[CH2:53][CH2:54][NH:55]2)([O-:50])=[O:49].C(N(CC)CC)C>CN(C=O)C.O>[N+:48]([C:51]1[CH:59]=[CH:58][CH:57]=[C:56]2[C:52]=1[CH2:53][CH2:54][N:55]2[C:45]([C:41]1[N:42]=[CH:43][N:44]=[C:39]([N:36]2[CH2:37][CH2:38][CH:33]([N:25]3[C:26]4[C:27](=[N:28][CH:29]=[CH:30][CH:31]=4)[NH:32][C:24]3=[O:23])[CH2:34][CH2:35]2)[CH:40]=1)=[O:46])([O-:50])=[O:49]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 132366324-Nitro-2,3-dihydro-1H-indoleHCID 583866966-[4-(2-Oxo-2,3-dihydroimidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]pyrimidine-4-carboxylic acid

Product 1

HCID 583863791-{1-[6-(4-Nitro-2,3-dihydroindole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydroimidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

150 mg (0.470 mmol) TBTU were added to 150 mg (0.44 mmol) 6-[4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid, 75 mg (0.46 mmol) 4-nitro-2,3-dihydro-1H-indole, 100 μL (0.712 mmol) triethylamine in 1.5 mL DMF and the mixture was stirred overnight at RT. The reaction mixture was poured onto 30 mL water. The aqueous phase was extracted with DCM (3×20 mL). The combined organic phases were dried on magnesium sulphate, filtered and evaporated down i. vac. The residue was dissolved in 3 mL DMF, filtered through a syringe filter and purified by preparative HPLC. The product fractions were combined and lyophilised.

Workup

  1. extractionThe aqueous phase was extracted with DCM (3×20 mL)
  2. customThe combined organic phases were dried on magnesium sulphate
  3. filtrationfiltered
  4. customevaporated down i
  5. dissolutionThe residue was dissolved in 3 mL DMF
  6. filtrationfiltered through a syringe
  7. filtrationfilter
  8. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-cd8e6db8c4a94aeaa3ad584dd44fa0b7
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

Loading…