Triethylamine → HCID 178425220, compound

HRID 1526992Notes

Reaction equation

HRID 1526992 reaction equation
[CH3:1][C:2]1[N:10]([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:19]([OH:21])=O.C[NH3+].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.[NH2:55][CH2:56][C:57]1[C:58]([OH:65])=[N:59][C:60]([CH3:64])=[CH:61][C:62]=1[CH3:63].C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[OH:65][C:58]1[C:57]([CH2:56][NH:55][C:19]([C:3]2[C:4]3=[N:5][CH:6]=[CH:7][CH:8]=[C:9]3[N:10]([CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH3:12])[C:2]=2[CH3:1])=[O:21])=[C:62]([CH3:63])[CH:61]=[C:60]([CH3:64])[N:59]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 866211442-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate MethanaminiumHCID 117778902HCID 117778902, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425220HCID 178425220, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 2-methyl-1-(1-phenylethyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (20 mg, 0.11 mmol), 2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate Methanaminium (50 mg, 0.13 mmol), 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (19 mg, 0.12 mmol) and triethylamine (23 mg, 0.22 mmol) in N,N-dimethylformamide (5 mL) was stirred for 12 hours. After the reaction was completed, the reaction was diluted with ethyl acetate (100 mL), and washed with water (20 mL×3) and brine (20 mL), dried over anhydrous sodium sulfate and concentrated to give the residue, which was purified by column chromatography (silica gel, dichloromethane/methanol=30:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-2-methyl-1-(1-phenylethyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (15 mg, 33%). LRMS (M+H+) m/z: calcd 415.20. found 415. HPLC Purity (214 nm): 99%. 1H NMR (300 MHz, d6-DMSO) δ 11.46 (s, 1H), 9.49 (t, J1=4.2 Hz, J2=8.1 Hz, 1H), 8.28 (d, J=3.6 Hz, 1H), 7.50 (d, J=6.3 Hz, 1H), 7.36-7.27 (m, 3H), 7.16 (d, J=5.7 Hz, 1H), 7.03-7.00 (m, 1H), 6.03 (m, 1H), 5.85 (s, 1H), 4.37 (s, 2H), 2.89 (s, 3H), 2.50 (s, 3H), 2.10 (s, 3H), 1.89 (d, J=5.4 Hz, 3H).

Workup

  1. washwashed with water (20 mL×3) and brine (20 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customto give the residue, which
  5. customwas purified by column chromatography (silica gel, dichloromethane/methanol=30:1)

Sources & evidence

ORD record
ord-04cdb242af17474f9301c7ff9a4f21d3
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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