Boron Trichloride → HCID 136372776, compound

HRID 1821012Notes

Reaction equation

HRID 1821012 reaction equation
B(Cl)(Cl)Cl.[C:5]([C:7]1[CH:8]=[C:9]([C:17]2[S:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:24][C:23]=3[CH3:35])[N:18]=2)[CH:10]=[CH:11][C:12]=1[O:13]C(C)C)#[N:6]>C(Cl)Cl>[C:5]([C:7]1[CH:8]=[C:9]([C:17]2[S:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:24][C:23]=3[CH3:35])[N:18]=2)[CH:10]=[CH:11][C:12]=1[OH:13])#[N:6]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 68892372HCID 68892372, compound

Product 1

HCID 136372776HCID 136372776, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Boron trichloride (1 M in CH2Cl2, 3 mL was added to a solution of ethyl 3-(4-(5-(3-cyano-4-isopropyloxyphenyl)-1,3,4-thiadiazol-3-yl)-3-methylphenyl)propanoate (0.6 mmol, from Step C) in methylene chloride (40 mL) at 0° C. The reaction mixture was allowed to warm to rt over 4 h and then was stirred at rt for 16 h. The reaction mixture was diluted with methylene chloride (50 mL) and washed with water (50 mL). The organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography eluting with EtOAc yielded 0.12 g of the title compound. 1H NMR (500 MHZ, CDCl3) δ 1H NMR (500 MHZ, CDCl3) δ 8.17 (s, 1H), 8.13 (s, 1H), 7.68 (s, 1H), 7.24 (s, 1H), 7.20-7.24 (m, 2H), 4.14-4.23 (m, 2H), 2.98-3.08 (m, 2H), 2.68-2.78 (m, 2H), 2.64 (s, 3H), 1.30 (t, J=7.1, 3H); ESI-MS (m/z) 394.2; HPLC A: 2.71 min.

Workup

  1. washwashed with water (50 mL)
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washSilica gel chromatography eluting with EtOAc

Sources & evidence

ORD record
ord-ffb54684f0ba4fbdbdc6c676e3e9e911
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

Loading…