Diisopropylethylamine → HCID 178468671, compound

HRID 1157771Notes

Reaction equation

HRID 1157771 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:10][N:9]=[C:8]([C:11]2[N:12]=[CH:13][C:14]([F:25])=[C:15]3[C:19]([C:20](=[O:24])[C:21](O)=[O:22])=[CH:18][NH:17][C:16]=23)[CH:7]=1)=[O:5])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[C:57]1([C:63]2[C:67]([N:68]3[CH2:73][CH2:72][NH:71][CH2:70][CH2:69]3)=[CH:66][NH:65][N:64]=2)[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>CN(C=O)C>[F:25][C:14]1[CH:13]=[N:12][C:11]([C:8]2[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[NH:10][N:9]=2)=[C:16]2[NH:17][CH:18]=[C:19]([C:20](=[O:24])[C:21](=[O:22])[N:71]3[CH2:72][CH2:73][N:68]([C:67]4[C:63]([C:57]5[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=5)=[N:64][NH:65][CH:66]=4)[CH2:69][CH2:70]3)[C:15]=12

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59511177HCID 59511177, compoundHCID 178420169HCID 178420169, compound

Product 1

HCID 178468671HCID 178468671, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(7-(5-(ethoxycarbonyl)-1H-pyrazol-3-yl)-4-fluoro-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid (0.017 g, 0.049 mmol) in DMF (1.5 mL) was added TBTU (0.017 g, 0.054 mmol), diisopropylethylamine (0.15 mL), and 1-(3-phenyl-1H-pyrazol-4-yl)piperazine (0.011 g, 0.049 mmol). The mixture was stirred under N2 at rt for 14.5 h and was quenched with 10 mL of H2O. The solvent was removed under reduced pressure, and the residue was dissolved in DMF. The DMF solution was passed though a plug of celite to remove solids, and the DMF solution was purified by prep HPLC to give the title compound as a white solid (13.3 mg). LCMS: m/e 557.4 (M+H)+, ret time 1.79 min (method 1). 1H NMR (500 MHz, MeOD) δ ppm 8.44 (s, 1H) 8.31 (d, J=2.44 Hz, 1H) 7.95 (d, J=7.32 Hz, 2H) 7.63 (s, 1H) 7.56 (s, 1H) 7.46 (t, J=7.63 Hz, 2H) 7.36 (t, J=7.48 Hz, 1H) 4.46 (q, J=7.22 Hz, 2H) 3.88-3.92 (m, 2H) 3.65-3.70 (m, 2H) 3.00-3.04 (m, 2H) 2.91-2.95 (m, 2H) 1.45 (t, J=7.02 Hz, 3H).

Workup

  1. customwas quenched with 10 mL of H2O
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in DMF
  4. customto remove solids
  5. customthe DMF solution was purified by prep HPLC

Sources & evidence

ORD record
ord-3b4dd71092ad4f879752920c28599ead
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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