Hydrochloric Acid → HCID 131728150, compound

HRID 13001Notes

Reaction equation

HRID 13001 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:14][C:15]1[C:16]2[C:21]([CH:22]=[C:23]3[C:28]=1[CH:27]=[CH:26][CH:25]=[CH:24]3)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH3:13])(C)(C)C.[ClH:30]>C(O)C>[ClH:30].[CH:27]1[C:28]2[C:23](=[CH:22][C:21]3[C:16]([C:15]=2[CH2:14][N:11]([CH2:12][CH3:13])[CH2:10][CH2:9][CH2:8][NH2:7])=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11596318HCID 11596318, compound

Product 1

HCID 131728150HCID 131728150, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 12b (400 mg, 1.02 mmole) was dissolved in absolute ethanol (13 mL) and stirred at 0° C. for 10 minutes. A 4N HCl solution (22 mL) was added to the reaction mixture dropwise and stirred at 0° C. for 20 minutes and then at room temperature overnight. The solution was concentrated in vacuo to give 12c as a yellow solid in 90% yield. 1H NMR (D2O) δ 8.42 (s, 1H), 8.0 (m, 4H), 7.71 (m, 2H), 7.61 (m, 2H), 4.87 (s, 2H), 3.34 (br q, 2H), 3.14 (br t, 2H), 2.81 (t, 2H), 2.00 (q, 2H), 1.40 (t, 3H); 13C NMR (D2O): δ 133.8, 133.3 (3C), 132.4 (2C), 130.7 (2C), 128.2 (2C), 125.1 (2C), 121.5 (2C), 52.0, 51.9, 39.2 (2C), 24.5, 11.3. HRMS (FAB) calcd for C20H24N2.2HCl (M+H−2HCl)+ 293.2012, Found 293.2009.

Workup

  1. stirringstirred at 0° C. for 20 minutes
  2. customat room temperature
  3. customovernight
  4. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-328fe4db736945148e38e6f2a016ee86
Source dataset
uspto-grants-2010_06
Patent number
US07728041B2

Reaction notes

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