Hydrochloric Acid → HCID 178478751, compound

HRID 1922400Notes

Reaction equation

HRID 1922400 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([NH:23][C:24]([C:26]4[S:27][CH:28]=[CH:29][CH:30]=4)=[NH:25])=[CH:20][CH:21]=3)[CH2:16][CH2:15][CH2:14]2)[CH2:9]1)=O)(C)(C)C.[ClH:31]>CO>[ClH:31].[ClH:31].[NH:8]1[CH2:12][CH2:11][CH:10]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([NH:23][C:24]([C:26]4[S:27][CH:28]=[CH:29][CH:30]=4)=[NH:25])=[CH:20][CH:21]=3)[CH2:16][CH2:15][CH2:14]2)[CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178452051HCID 178452051, compound

Product 1

HCID 178478751HCID 178478751, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of tert-butyl-3-(6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)pyrrolidine-1-carboxylate (150 mg, 0.35 mmol) in 5 mL methanol was treated with 10 mL 1N HCl then heated at 70° C. for 30 minutes. The solution was concentrated and dried under reduced pressure to give a yellow solid. This solid was triturated with 5% MeOH/95% Et2O. The yellow solid was collected and dried under reduced pressure. Yield: 125 mg (89.3%). 1H-NMR (DMSO-d6) δ 11.23 (s, 1H), 9.78 (brs, 1H), 9.65 (brs, 1H, 9.59 (brs, 1H), 8.61 (s, 1H), 8.15-8.14 (m, 2H), 7.36 (pseudo t, J=4.5 Hz, 1H), 7.09-6.88 (m, 3H), 4.76-4.66 (m, 1H), 3.39-3.06 (m, 6H), 2.72 (t, J=5.4 Hz, 2H), 2.16-2.01 (m, 2H), 1.87-1.83 (m, 2H). MS (EI): 327.2 (M+1). ESI-HRMS calculated for C18H23N4S (MH+): 327.1637, Observed: 327.1649.

Workup

  1. concentrationThe solution was concentrated
  2. customdried under reduced pressure
  3. customto give a yellow solid
  4. customThis solid was triturated with 5% MeOH/95% Et2O
  5. customThe yellow solid was collected
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-15a24f261876499888d140d0bf5af7ce
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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