Hydrochloric Acid → HCID 178511882, compound

HRID 1922454Notes

Reaction equation

HRID 1922454 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[NH:29])[NH:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH:17]1[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]1)[CH2:12][CH2:11]2.Cl>CO>[NH:19]1[CH2:20][CH2:21][CH:17]([N:13]2[C:14]3[C:10](=[CH:9][C:8]([NH:7][C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)=[NH:29])=[CH:16][CH:15]=3)[CH2:11][CH2:12]2)[CH2:18]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178452048HCID 178452048, compound

Product 1

HCID 178511882HCID 178511882, compoundYield 113.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound 6 (0.35 g, 0.848 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 49 (0.3 g, 92%) as a solid. 1H NMR (DMSO-d6) δ11.25 (s, 1H), 9.82-9.60 (m, 3H), 8.63 (s, 1H), 8.15-8.13 (m, 2H), 7.36 (t, 1H, J=4.5 Hz), 7.12-7.06 (m, 2H), 6.68 (d, 1H, J=8.4 Hz), 4.39-4.35 (m, 1H), 3.56-3.06 (m, 6H), 2.96 (t, 2H, J=8.1 Hz), 2.18-2.00 (m, 2H); ESI-MS (m/z, %): 313 (MH+, free base, 100), 244 (61); ESI-HRMS calculated for C17H21N4S (MH+, free base), calculated: 313.1481; observed: 313.1473; HPLC-purity: 94.05% 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-389f32f2190f435d934c67e2613dd0f6
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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