Hydrochloric Acid → HCID 178478752, compound

HRID 1922473Notes

Reaction equation

HRID 1922473 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[NH:30])[NH:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH:17]1[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]1)[CH2:12][CH2:11]2.[ClH:31]>CO>[ClH:31].[ClH:31].[NH:20]1[CH2:21][CH2:22][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:30])=[CH:16][CH:15]=3)[CH2:11][CH2:12]2)[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178452049HCID 178452049, compound

Product 1

HCID 178478752HCID 178478752, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound 6 (0.23 g, 0.539 mmol) in methanol (10 mL) was treated with 1 N HCl solution (10 mL) and the resulting mixture was refluxed for 30 min. The reaction was brought to room temperature and solvent was evaporated. The crude was dissolved into water (10 mL), filtered and washed with water (2×5 mL). The combined water layer was evaporated to obtain compound 54 (0.18 g, 84%) as dihydrochloride salt. 1H NMR (DMSO-d6) δ 11.21 (s, 1H), 9.64 (s, 1H), 9.20-9.04 (m, 2H), 8.60 (s, 1H), 8.15-8.12 (m, 2H), 7.36 (t, 1H, J=4.5 Hz), 7.11-7.03 (m, 2H), 6.66 (d, 1H, J=8.4 Hz), 3.86-3.74 (m, 1H), 3.44-3.32 (m, 4H), 3.06-2.92 (m, 4H), 1.98-1.78 (m, 4H); ESI-MS (m/z, %) 327 (MH+, 100), 244 (81); ESI-HRMS calculated for C18H23N4S (MH+), calculated: 327.1637; observed: 327.1636; HPLC purity: 98.86% by area.

Workup

  1. temperaturethe resulting mixture was refluxed for 30 min
  2. customwas brought to room temperature
  3. customsolvent was evaporated
  4. dissolutionThe crude was dissolved into water (10 mL)
  5. filtrationfiltered
  6. washwashed with water (2×5 mL)
  7. customThe combined water layer was evaporated

Sources & evidence

ORD record
ord-fca1e9bcbeda4821a766757fe4c4f45d
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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