Hydrochloric Acid → HCID 178464379, compound

HRID 1922491Notes

Reaction equation

HRID 1922491 reaction equation
[CH2:1]([N:3]([CH2:11][CH2:12][N:13]1[C:22]2[C:17](=[CH:18][C:19]([NH:23][C:24]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[NH:25])=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1)C(=O)OC(C)(C)C)[CH3:2].Cl>CO>[CH2:1]([NH:3][CH2:11][CH2:12][N:13]1[C:22]2[C:17](=[CH:18][C:19]([NH:23][C:24]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[NH:25])=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178464380HCID 178464380, compound2×

Product 1

HCID 178464379HCID 178464379, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of tert-butyl ethyl(2-(6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate (compound 8, 115 mg, 0.268 mmol) in HPLC grade methanol (10 mL) was treated with 2N aq. HCl (1.35 mL, 2.7 mmol) and the mixture heated to reflux for 90 minutes. After cooling to room temperature, the solution was concentrated and dried briefly on high-vac pump. The residue was purified directly on silica gel eluting with 10% 2M NH3 in methanol/90% dichloromethane to yield a yellow solid, 9 (78 mg, 88%). 1H-NMR (DMSO-d6) δ 7.66 (d, 1H, J=3.0 Hz), 7.54 (dd, 1H, J=5.0, 0.9 Hz), 7.06 (dd, 1H, J=5.0, 3.7 Hz), 6.59-6.52 (m, 2H), 6.47 (br s, 1H), 6.21 (br s, 2H), 3.32-3.20 (m, 4H), 2.70-2.64 (m, 4H), 2.56 (q, 2H, J=7.1 Hz), 1.88-1.80 (m, 2H), 1.04 (t, 3H, J=7.0 Hz). MS (ESI+): 329 (MH+, 100), 258 (100); ESI-HRMS calculated for C18H25N4S (MH+): 329.1794; observed: 329.1798.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 90 minutes
  3. concentrationthe solution was concentrated
  4. customdried briefly on high-vac pump
  5. customThe residue was purified directly on silica gel eluting with 10% 2M NH3 in methanol/90% dichloromethane

Sources & evidence

ORD record
ord-faaefd89ff24469f87aebdf837069b7e
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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