1-(2-Morpholinoethyl)-1,2,3,4-tetrahydroquinolin-6-amine → HCID 178483703, compound

HRID 1922507Notes

Reaction equation

HRID 1922507 reaction equation
CN(C)CCN1C2C(=CC([N+]([O-])=O)=CC=2)CC1.[H][H].[N+](C1C=C2C(=CC=1)N(CCN1CCCC1)CC2)([O-])=O.O1CCN(CCN2C3C(=CC(N)=CC=3)CCC2)CC1.O=[C:59]1[N:65]([CH2:66][CH2:67][N:68]2[CH2:73]CCC[CH2:69]2)[C:64]2[CH:74]=[CH:75][C:76]([NH:78][C:79]([C:81]3[S:82][CH:83]=[CH:84][CH:85]=3)=[NH:80])=[CH:77][C:63]=2[CH2:62]CC1>C(O)C.C([O-])(O)=O.[Na+].[Pd]>[CH3:73][N:68]([CH3:69])[CH2:67][CH2:66][N:65]1[C:64]2[C:63](=[CH:77][C:76]([NH:78][C:79]([C:81]3[S:82][CH:83]=[CH:84][CH:85]=3)=[NH:80])=[CH:75][CH:74]=2)[CH2:62][CH2:59]1

Participants

9

Reactant 5

HCID 284191151-(2-Morpholinoethyl)-1,2,3,4-tetrahydroquinolin-6-amineHCID 58289996HCID 58289996, compoundHCID 598071295-Nitro-1-(2-(pyrrolidin-1-yl)ethyl)indolineHCID 178418361HCID 178418361, compoundHCID 178511874HCID 178511874, compound

Product 1

HCID 178483703HCID 178483703, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of compound 2 (183 mg, 0.778 mmol) and Pd—C (82 mg, 0.078 mmol, 10% wt) in dry ethanol (5 mL) was purged with hydrogen gas. The reaction was stirred at room temperature over night under hydrogen atm. (balloon pressure). Then the reaction mixture was filtered through a celite pad and washed with ethanol (35 mL). The filtrate (compound 3) was treated with imidate 4 (444 mg, 1.559 mmol) and stirred over night at room temperature. The reaction was diluted with saturated NaHCO3 solution (50 mL) and product was extracted into CH2Cl2 (3×25 mL). The combined organic layers were dried (Na2SO4) and concentrated. The residue was subjected to flash chromatography on silica gel: 2% methanol: 98% CH2Cl2 followed by 2.5% 2M NH3 in methanol: 97.5% CH2Cl2 followed by 5% 2M NH3 in methanol: 95% CH2Cl2, to give a greenish/yellow solid (90 mg, yield). 1H-NMR (DMSO-d6) δ 7.68 (d, J=2.7 Hz, 1H), 7.56 (dd, J=5.1, 1.2 Hz, 1H), 7.07 (dd, J=3.6, 5.1 Hz, 1H), 6.62 (s, 1H), 6.55-6.46 (m, 2H), 6.28 (s, 2H), 3.32-3.27 (m, 2H), 3.09 (t, J=6.6 Hz, 2H), 2.84 (t, J=8.1 Hz, 2H), 2.45 (t, J=6.9 Hz, 2H), 2.20 (s, 6H). ESI-MS (m/z, %): 315 (MH+, 100), 244 (29), 127 (38); ESI-HRMS calculated for C17H23N4S (MH+): calculated 315.1637, Observed: 315.1645: HPLC purity: 95.3%.

Workup

  1. filtrationThen the reaction mixture was filtered through a celite pad
  2. washwashed with ethanol (35 mL)
  3. stirringstirred over night at room temperature
  4. extractionwas extracted into CH2Cl2 (3×25 mL)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated
  7. custom95% CH2Cl2, to give
  8. customa greenish/yellow solid (90 mg, yield)

Sources & evidence

ORD record
ord-a5b0124acf824c5ca4b788d8c938fbaf
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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