Hydrochloric Acid → HCID 178485448, compound

HRID 470672Notes

Reaction equation

HRID 470672 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C@@H:14]2[C@@:25]3([C:33]4[C:28](=[CH:29][C:30]([Cl:34])=[CH:31][CH:32]=4)[NH:27][C:26]3=[O:35])[C:17]3([CH2:22][CH2:21][C:20]([CH3:24])([CH3:23])[CH2:19][CH2:18]3)[NH:16][C@H:15]2[C:36](=[O:45])[NH:37][C@H:38]2[CH2:43][CH2:42][C@H:41]([OH:44])[CH2:40][CH2:39]2)[CH:13]=1)[C:7](OC)=[O:8].Cl.Cl.CN.[CH2:50]([N:52](CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.C(=O)(O)[O-].[Na+]>CO>[Cl:34][C:30]1[CH:29]=[C:28]2[C:33]([C@@:25]3([C@@H:14]([C:12]4[CH:11]=[C:6]([C:7](=[O:8])[NH:52][CH3:50])[CH:5]=[C:4]([Cl:3])[CH:13]=4)[C@H:15]([C:36]([NH:37][C@H:38]4[CH2:39][CH2:40][C@H:41]([OH:44])[CH2:42][CH2:43]4)=[O:45])[NH:16][C:17]43[CH2:18][CH2:19][C:20]([CH3:23])([CH3:24])[CH2:21][CH2:22]4)[C:26](=[O:35])[NH:27]2)=[CH:32][CH:31]=1

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6364545Methylamine hydrochlorideHCID 178498035HCID 178498035, compound

Product 1

HCID 178485448HCID 178485448, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

1N sodium hydroxide solution (0.19 ml, 0.19 mmol) was added to a methanol (4 ml) solution of the compound (81 mg, 0.13 mmol) obtained in Step 4 above and the resulting mixture was stirred at 50° C. for 4 hours. The reaction mixture was neutralized by addition of 1N hydrochloric acid and then the resulting mixture was concentrated under reduced pressure. Dichloromethane (4 ml) was added to the residue, then methylamine hydrochloride (26 mg, 0.39 mmol), triethylamine (0.11 ml, 0.77 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (74 mg, 0.39 mmol) were added and the resulting mixture was stirred at room temperature for 24 hours. Saturated sodium bicarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and then the residue was purified by NH-silica gel column chromatography [methanol:ethyl acetate=5:95 (v/v)] to give 42 mg (52%) of the title compound as a colorless solid.

Workup

  1. concentrationthe resulting mixture was concentrated under reduced pressure
  2. additionDichloromethane (4 ml) was added to the residue
  3. stirringthe resulting mixture was stirred at room temperature for 24 hours
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by NH-silica gel column chromatography [methanol:ethyl acetate=5:95 (v/v)]

Sources & evidence

ORD record
ord-07aa418f83e646c78b75ce2fbe426e25
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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