Triethylamine → HCID 58386575, compound

HRID 74530

Reaction equation

HRID 74530 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]([OH:47])=O)[CH:40]=2)[CH2:35][CH2:34]1.[N+:48]([C:51]1[CH:52]=[C:53]2[C:57](=[CH:58][CH:59]=1)[NH:56][CH2:55][CH2:54]2)([O-:50])=[O:49].C(N(CC)CC)C>CN(C=O)C.O>[N+:48]([C:51]1[CH:52]=[C:53]2[C:57](=[CH:58][CH:59]=1)[N:56]([C:45]([C:41]1[N:42]=[CH:43][N:44]=[C:39]([N:36]3[CH2:37][CH2:38][CH:33]([N:25]4[C:26]5[C:27](=[N:28][CH:29]=[CH:30][CH:31]=5)[NH:32][C:24]4=[O:23])[CH2:34][CH2:35]3)[CH:40]=1)=[O:47])[CH2:55][CH2:54]2)([O-:50])=[O:49]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 362195-NitroindolineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 583866966-[4-(2-Oxo-2,3-dihydroimidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]pyrimidine-4-carboxylic acid

Product 1

HCID 58386575HCID 58386575, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

150 mg (0.47 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) 5-nitro-2,3-dihydro-1H-indole, 100 μL and (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 precipitated product was suction filtered and dried at 50° C. in the CAD.

Workup

  1. filtrationfiltered
  2. customdried at 50° C. in the CAD

Sources & evidence

ORD record
ord-82f55e6c994141e0a18f1092baf0e473
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Linked notes

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