Triethylamine → HCID 178493291, compound

HRID 1157751Notes

Reaction equation

HRID 1157751 reaction equation
[C:1]([C:4]([C:6]1[C:14]2[C:9](=[N+:10]([O-:17])[CH:11]=[CH:12][C:13]=2[O:15][CH3:16])[NH:8][CH:7]=1)=[O:5])([OH:3])=O.C(N(CC)CC)C.[C:25]1([N:31]2[C:35]([N:36]3[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]3)=[N:34][N:33]=[N:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.O>[CH3:16][O:15][C:13]1[CH:12]=[CH:11][N+:10]([O-:17])=[C:9]2[NH:8][CH:7]=[C:6]([C:4](=[O:5])[C:1](=[O:3])[N:39]3[CH2:40][CH2:41][N:36]([C:35]4[N:31]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[N:32]=[N:33][N:34]=4)[CH2:37][CH2:38]3)[C:14]=12

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 38255781-(1-Phenyl-1H-tetrazol-5-YL)piperazineHCID 178493292HCID 178493292, compound

Product 1

HCID 178493291HCID 178493291, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of the solid containing 3-(carboxycarbonyl)-4-methoxy-1H-pyrrolo[2,3-b]pyridine 7-oxide from above (200 mg, 0.84 mmol), triethylamine (0.5 mL, sssss), 1-(1-phenyl-1H-tetrazol-5-yl)piperazine (234 mg, 1.01 mmol) and TBTU (404 mg, 1.26 mmol) was stirred at rt in DMF (1 mL) for 24 h. H2O was added and the reaction mixture was concentrated under reduced pressure. The residue was purified using reverse phase prep HPLC to afford the title compound as a white solid (15 mg, 4%). 1H NMR (500 MHz, CDCl3) δ ppm 3.32 (s, 2H) 3.37 (s, 2H) 3.56 (s, 2H) 3.79 (s, 2H) 4.13 (s, 3H) 6.83 (d, J=7.32 Hz, 1H) 7.53 (d, J=6.71 Hz, 1H) 7.54-7.60 (m, 3H) 8.16 (s, 1H) 8.34 (d, J=6.71 Hz, 1H). LCMS: m/e 449 (M+H)+, ret time 0.99 min (method 2).

Workup

  1. additionA mixture of the solid
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified

Sources & evidence

ORD record
ord-581a1c12c1834b06989cd158ce5320e8
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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