NoName_3327 → 6-[4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid(1H-indazol-4-yl)-amide

HRID 74703

Reaction equation

HRID 74703 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[N:3]1[CH:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:22]=[CH:21][N:20]=[C:19]([C:23]([OH:25])=O)[CH:18]=2)[CH2:13][CH2:12]1.[NH:26]1[C:34]2[C:29](=[C:30]([NH2:35])[CH:31]=[CH:32][CH:33]=2)[CH:28]=[N:27]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[NH:26]1[C:34]2[C:29](=[C:30]([NH:35][C:23]([C:19]3[CH:18]=[C:17]([N:14]4[CH2:15][CH2:16][CH:11]([N:3]5[C:4]6[C:5](=[N:6][CH:7]=[CH:8][CH:9]=6)[NH:10][C:2]5=[O:1])[CH2:12][CH2:13]4)[N:22]=[CH:21][N:20]=3)=[O:25])[CH:31]=[CH:32][CH:33]=2)[CH:28]=[N:27]1

Participants

5

Reactant 3

HCID 413085NoName_3327HCID 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 673385426-[4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid(1H-indazol-4-yl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.29 mmol) 6-[4-(2-oxo-2,3-dihydroimidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid and 39 mg (0.29 mmol) 1H-indazole-4-ylamine in 87 mL (0.62 mmol) TEA and 1.5 mL DMF were combined with 104 mg (0.32 mmol) TBTU and stirred overnight at RT. Then the reaction mixture was purified by preparative HPLC-MS. The product-containing fractions were combined and freeze-dried.

Workup

  1. customThen the reaction mixture was purified by preparative HPLC-MS
  2. customfreeze-dried

Sources & evidence

ORD record
ord-b5531eca3e51478f8e8aeef3b837b76d
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Linked notes

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