1,2-Dichloroethane → HCID 89962092, compound

HRID 877432Notes

Reaction equation

HRID 877432 reaction equation
C(Cl)CCl.[CH3:5][C:6]1([CH3:22])[C:10]([CH3:12])([CH3:11])[O:9][B:8]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=2)[O:7]1.[CH3:23][O:24][CH2:25][CH2:26][NH:27][CH3:28].C1C=C2N=NN(O)C2=CC=1.O>O.CN(C=O)C>[CH3:23][O:24][CH2:25][CH2:26][N:27]([CH3:28])[C:17](=[O:19])[C:16]1[CH:15]=[CH:14][C:13]([B:8]2[O:9][C:10]([CH3:11])([CH3:12])[C:6]([CH3:5])([CH3:22])[O:7]2)=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 300977(2-Methoxyethyl)(methyl)amineHCID 27346214-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 89962092HCID 89962092, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

EDC (310 mg, 1.6 mmol) was added to DMF (4 mL) solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (200 mg, 0.81 mmol), 2-methoxy-N-methylethanamine (144 mg, 1.6 mmol), TEA (0.23 mL, 1.6 mmol) and HOBT hydrate (247 mg, 1.60 mmol). After 3 days at room temperature, the reaction mixture was diluted in water (15 mL), extracted with DCM (3×10 mL), the combined organic portions dried over Na2SO4, filtered, concentrated under reduced pressure and purified by reverse phase HPLC (Phenomemenx Luna AXIA 5 micron C18, 21.2×100, UV at 220 nm, 10 to 70% B over 30 minutes with 10 minute hold time, solvent A: 90% water/ACNl/0.1% TFA, solvent B:90% ACN/water/0.1% TFA, Flow rate 20 mL/min; detector at 254) to isolate Compound B172a (47 mg, 18% yield) as a clear oil. HPLC: RT=0.96 min (LCMS Method M). MS (ES): m/z=319.7 [M+H]+. 1H NMR (500 MHz, CHLOROFORM-d) δ 9.45-8.71 (m, 1H), 7.85 (d, J=7.2 Hz, 2H), 7.40 (d, J=8.0 Hz, 2H), 3.89-3.64 (m, 2H), 3.42 (d, J=12.1 Hz, 3H), 3.34-3.12 (m, 3H), 3.04 (s, 2H), 1.36 (s, 12H).

Workup

  1. extractionextracted with DCM (3×10 mL)
  2. dry with materialthe combined organic portions dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. custompurified by reverse phase HPLC (Phenomemenx Luna AXIA 5 micron C18, 21.2×100, UV at 220 nm, 10 to 70% B over 30 minutes with 10 minute hold time, solvent A: 90% water/ACNl/0.1% TFA, solvent B:90% ACN/water/0.1% TFA, Flow rate 20 mL/min; detector at 254)
  6. customto isolate Compound B172a (47 mg, 18% yield) as a clear oil

Sources & evidence

ORD record
ord-dab312af232a4dfcaed9262bbda104eb
Source dataset
uspto-grants-2015_03
Patent number
US08987314B2

Reaction notes

Loading…