Hydrochloric Acid → HCID 178511872, compound

HRID 1922451Notes

Reaction equation

HRID 1922451 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[NH:31])[NH:7][C:8]1[CH:30]=[CH:29][C:11]2[N:12]([CH:17]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]3)[CH2:13][CH2:14][CH2:15][CH2:16][C:10]=2[CH:9]=1.Cl>CO>[NH:19]1[CH2:20][CH2:21][CH:17]([N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C:10]3[CH:9]=[C:8]([NH:7][C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)=[NH:31])[CH:30]=[CH:29][C:11]2=3)[CH2:18]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178452052HCID 178452052, compound

Product 1

HCID 178511872HCID 178511872, compoundYield 113.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound 4 (0.8 g, 1.815 mmol) in methanol (10 mL) was treated with 1 N HCl (10 mL) and the resulting mixture was refluxed for 30 minutes. The reaction was brought to room temperature and solvent was evaporated. The crude product was dissolved into water (10 mL), filtered and washed. Water was evaporated to obtain compound 48 (0.7 g, 93%) as a solid. 1H NMR (DMSO-d6) δ 11.44 (s, 1H), 9.78-9.65 (m, 3H), 8.78 (s, 1H), 8.17-8.15 (m, 2H), 7.37 (t, 1H, J=4.2 Hz), 7.20-7.08 (m, 3H), 3.50-3.40 (m, 1H), 3.38-3.26 (m, 1H), 3.17-2.90 (m, 4H), 2.76 (brt, 2H), 2.30-2.20 (m, 1H), 2.00-1.90 (m, 1H), 1.70-1.50 (m, 4H); ESI-MS (m/z, %): 341 (MH+, 38), 272 (100); ESI-HRMS calculated for C19H25N4S (MH+, free base), calculated: 341.1794; observed: 341.1801; HPLC-purity: 98.20% by area.

Workup

  1. temperaturethe resulting mixture was refluxed for 30 minutes
  2. customwas brought to room temperature
  3. customsolvent was evaporated
  4. dissolutionThe crude product was dissolved into water (10 mL)
  5. filtrationfiltered
  6. washwashed
  7. customWater was evaporated

Sources & evidence

ORD record
ord-4f4fbd64bfed4c33abadda656f789237
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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