Hydrochloric Acid → HCID 10158751, compound

HRID 354139Notes

Reaction equation

HRID 354139 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([N:12]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:11])=[CH:5][CH:4]=1.[CH:27](Br)([CH3:29])[CH3:28].CCN(C(C)C)C(C)C.C(=O)([O-])O.[Na+].Cl>C(#N)C.C(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([N:12]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=2)[CH:13]2[CH2:18][CH2:17][N:16]([CH:27]([CH3:29])[CH3:28])[CH2:15][CH2:14]2)=[O:11])=[CH:7][CH:8]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 63582-BromopropaneHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 10270645HCID 10270645, compound

Product 1

HCID 10158751HCID 10158751, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

42ELH89 (0.25 g, 0.67 mmol, 1.0 eq) was transferred to a 4 ml vial and dissolved in acetonitrile (2 ml). Isopropyl bromide (0.25 g, 3.0 eq.) was added along with Hünigs base (0.87 g, 10.0 eq.). The vial was sealed and shaken for 4 days at 60° C. The reaction mixture was transferred to a separatory funnel with distilled water and CH2Cl2. The aqueous phase was made basic with sodium hydrogen carbonate and extracted with dichloromethane (3 times). The organic layers were collected and dried with sodium sulfate and concentrated, this resulted in a yellow oil. The product was purified by flash chromatography (3% MeOH in CH2Cl2). The resulting product was dissolved in dichloromethane (1 ml) and HCl (1 eq. 2 M HCl in ether) was added under stirring. The salt precipitated by addition of the dichloromethane solution into heptane. Concentration on the rotary evaporator returned the product as white crystals. Yield 101.2 mg (63%), UV/MS 94/96 (M+ 415), Rf 0.25 (3% MeOH/CH2Cl2).

Workup

  1. customThe vial was sealed
  2. extractionextracted with dichloromethane (3 times)
  3. customThe organic layers were collected
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. customthis resulted in a yellow oil
  7. customThe product was purified by flash chromatography (3% MeOH in CH2Cl2)
  8. dissolutionThe resulting product was dissolved in dichloromethane (1 ml)
  9. stirringunder stirring
  10. customThe salt precipitated by addition of the dichloromethane solution into heptane
  11. concentrationConcentration
  12. customon the rotary evaporator

Sources & evidence

ORD record
ord-30ccfbca50944918817bbbc8be836028
Source dataset
uspto-grants-2004_06
Patent number
US06756393B2

Reaction notes

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