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

HRID 74635Notes

Reaction equation

HRID 74635 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.[F:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][CH2:31][CH2:30]2.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[F:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[N:32]([C:23]([C:19]1[N:20]=[CH:21][N:22]=[C:17]([N:14]3[CH2:15][CH2:16][CH:11]([N:3]4[C:4]5[C:5](=[N:6][CH:7]=[CH:8][CH:9]=5)[NH:10][C:2]4=[O:1])[CH2:12][CH2:13]3)[CH:18]=1)=[O:25])[CH2:31][CH2:30]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27744635-FluoroindolineHCID 583866966-[4-(2-Oxo-2,3-dihydroimidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]pyrimidine-4-carboxylic acid

Product 1

HCID 426133011-{1-[6-(5-Fluoro-2,3-dihydroindole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.294 mmol) 6-[4-(2-oxo-2,3-dihydroimidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid, 42 mg (0.31 mmol) 5-fluoro-2,3-dihydro-1H-indole, 100 mg (0.311 mmol) TBTU and 45 μL (0.320 mmol) triethylamine in 10 mL DMF were stirred overnight at RT. The reaction mixture was evaporated down using the rotary evaporator. The residue was dissolved in 3 mL DMF and purified by preparative HPLC-MS. The product fractions were combined and lyophilised.

Workup

  1. customThe reaction mixture was evaporated down
  2. customthe rotary evaporator
  3. dissolutionThe residue was dissolved in 3 mL DMF
  4. custompurified by preparative HPLC-MS

Sources & evidence

ORD record
ord-afe99016cbe6430f9f112911bb28765a
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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