Triethylamine hydrochloride → HCID 178437525, compound

HRID 718624Notes

Reaction equation

HRID 718624 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([C:13]([C:28]4[CH:29]=[CH:30][C:31]([C:34]#[N:35])=[N:32][CH:33]=4)=[C:14]([C:16]#[C:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.[N-:36]=[N+:37]=[N-:38].[Na+].Cl.C(N(CC)CC)C>CN(C=O)C>[NH:36]1[C:34]([C:31]2[N:32]=[CH:33][C:28]([C:13]3[N:9]4[N:10]=[CH:11][CH:12]=[C:7]([N:4]5[CH2:3][CH2:2][O:1][CH2:6][CH2:5]5)[C:8]4=[N:15][C:14]=3[C:16]#[C:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)=[CH:29][CH:30]=2)=[N:35][N:38]=[N:37]1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 1177283575-(8-Morpholino-2-(2-(quinolin-2-yl)ethynyl)imidazo[1,2-b]pyridazin-3-yl)picolinonitrile

Product 1

HCID 178437525HCID 178437525, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of compound 39a (0.20 g, 0.44 mmol), sodium azide (50 mg, 0.77 mmol), and triethylamine hydrochloride (0.10 g, 0.73 mmol) in DMF (5 mL) was stirred at 100° C. for 1 h. After cooling to rt, the reaction was quenched with water (20 mL). The resulting mixture was extracted with DCM (2×30 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue obtained was purified by flash column chromatography on silica gel (MeOH:CH2Cl2 (1:50, v/v)) to obtain a residue, which was further purified by reverse phase Prep-HPLC. This resulted in the title compound 21 as a yellow solid. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 8.85-8.91 (m, 1H), 8.34 (d, J=8.7 Hz, 1H), 8.30-8.23 (m, 2H), 7.98-7.60 (m, 6H), 6.51 (d, J=6.0 Hz, 1H), 3.90-3.81 (m, 4H), 3.64-3.53 (m, 4H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C22H20N10O: 501.2 (M+H). Found: 501.2.

Workup

  1. customthe reaction was quenched with water (20 mL)
  2. extractionThe resulting mixture was extracted with DCM (2×30 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified by flash column chromatography on silica gel (MeOH:CH2Cl2 (1:50
  8. customv/v)) to obtain a residue, which
  9. customwas further purified by reverse phase Prep-HPLC

Sources & evidence

ORD record
ord-1bd5234e84cd4c7a8440970ef32679c4
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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