Hydrochloric Acid → HCID 46935693, compound

HRID 221202Notes

Reaction equation

HRID 221202 reaction equation
[Cl:1][C:2]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:3]=1[C:4]([NH:6][CH:7]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:8]1[CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]1)=[O:5].Cl.CCN(C(C)C)C(C)C.[CH2:40]([S:43](Cl)(=[O:45])=[O:44])[CH2:41][CH3:42]>O1CCOCC1>[Cl:1][C:2]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:3]=1[C:4]([NH:6][CH:7]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:8]1[CH2:9][N:10]([S:43]([CH2:40][CH2:41][CH3:42])(=[O:45])=[O:44])[CH2:11]1)=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 662791-Propanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 59534489HCID 59534489, compound

Product 1

HCID 46935693HCID 46935693, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 2 (500 mg, 1.15 mmol) in 1,4-dioxane (10 mL) was added 4N HCl in dioxane (5.0 mL) and stirred at room temperature for 2 h. The reaction was concentrated under vacuum. The residue was dissolved in CH2Cl2 (10 mL) and DIPEA (300 mg, 2.30 mmol) and added 1-propanesulfonyl chloride (164 mg, 1.15 mmol). The reaction was stirred at room temperature for 20 h. The reaction was concentrated under vacuum and the residue was purified by column chromatography (silica gel) using 0 to 35% EtOAc in hexanes to afford 3a as white solid (285 mg, 56%); 1H-nmr (300 MHz, CDCl3) δ 7.69 (d, J=8.5 Hz, 1H), 7.60-7.30 (m, 10H), 7.08 (d, J=8.5 Hz, 1H), 5.68 (dd, J=9.5, 6.5 Hz, 1H), 5.29 (br s, 1H), 3.76-3.71 (m, 2H), 3.55-3.35 (m, 2H), 3.19-3.01 (m, 2H), 2.69 (br s, 1H), 1.98-1.82 (m, 2H), 1.08 (t, J=7 Hz, 9H); LC-MS (214) 98%, 3.30 min, m/z 475 (MMeOH+).

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. dissolutionThe residue was dissolved in CH2Cl2 (10 mL)
  3. stirringThe reaction was stirred at room temperature for 20 h
  4. concentrationThe reaction was concentrated under vacuum
  5. customthe residue was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-d77403c88cda43aab648643c36dfde91
Source dataset
uspto-grants-2012_06
Patent number
US08207155B2

Reaction notes

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