Hydrochloric Acid → HCID 178457365, compound

HRID 1922494Notes

Reaction equation

HRID 1922494 reaction equation
C(OC(=O)[N:7]([CH:28]([CH3:30])[CH3:29])[CH2:8][CH2:9][N:10]1[C:19]2[C:14](=[CH:15][C:16]([NH:20][C:21]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[NH:22])=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)(C)(C)C.Cl>CO>[CH:28]([NH:7][CH2:8][CH2:9][N:10]1[C:19]2[C:14](=[CH:15][C:16]([NH:20][C:21]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[NH:22])=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)([CH3:30])[CH3:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178457366HCID 178457366, compound2×

Product 1

HCID 178457365HCID 178457365, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of tert-butyl-isopropyl(2-(6-(thiophene-2-carboximidamido)-3,4-dihydro-quinolin-1(2H)-yl)ethyl)carbamate (compound 6, 50 mg, 0.113 mmol) in HPLC grade methanol (10 mL) was treated with 2N aq. HCl (0.565 mL, 1.13 mmol) and the mixture heated to reflux for 2 hours then cooled to room temperature overnight. The solution was concentrated and dried briefly on high-vac pump. The residue was taken up in 7.5% 2M NH3 in methanol/92.5% dichloromethane (5 mL), reconcentrated then purified directly on silica gel eluting with 7.5% 2M NH3 in methanol/92.5% dichloromethane to yield a yellow solid, 61 (40 mg, quantitative). 1H-NMR (DMSO-d6) δ 7.66 (d, 1H, J=3.1 Hz), 7.54 (d, 1H, J=5.1 Hz), 7.06 (dd, 1H, J=5.0, 3.7 Hz), 6.61-6.50 (m, 2H), 6.47 (br s, 1H), 6.21 (br s, 2H), 3.30-3.18 (m, 4H), 2.79-2.70 (m, 1H), 2.70-2.61 (m, 4H), 1.88-1.80 (m, 2H), 0.97 (d, 6H, J=6.2 Hz). MS (ESI+): 343 (MH+, 100); ESI-HRMS calculated for C19H27N4S (MH+): 343.1950; observed: 343.1953.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 2 hours
  3. concentrationThe solution was concentrated
  4. customdried briefly on high-vac pump
  5. customreconcentrated then purified directly on silica gel eluting with 7.5% 2M NH3 in methanol/92.5% dichloromethane
  6. customto yield a yellow solid, 61 (40 mg, quantitative)

Sources & evidence

ORD record
ord-487240d9c61b4235931cd8f742bd7f47
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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