Thionyl Chloride → HCID 10976788, compound

HRID 1170546Notes

Reaction equation

HRID 1170546 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:9][C:4]=2[O:3][CH2:2]1.S(Cl)([Cl:17])=O>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][C:12]([Cl:17])=[O:14])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 648103-(Benzodioxol-5-yl)propionic acid

Product 1

HCID 10976788HCID 10976788, compound

Procedure

3-Benzo[1,3]dioxol-5-yl-propionic acid (2.50 g, 12.9 mmol) and thionyl chloride (20 mL, 274 mmol) were heated to 79° C. for 4 h then concentrated to afford 3-(benzo[d][1,3]dioxol-5-yl)propanoyl chloride as a brown oil. 2-(2-Imidazol-1-yl-6-methyl-pyrimidin-4-yl)-2-methyl-propylamine (100 mg, 0.432 mmol) and methylene chloride (20 mL) were added and the reaction mixture stirred at rt for about 2 h. The reaction mixture was filtered, filtrate washed with K2CO3 (100 mL, sat. aq.), and the organic layer was dried over Na2SO4. Filtration, concentration and purification using column chromatography gave 40 mg of 3-benzo[1,3]dioxol-5-yl-N-[2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-2-methyl-propyl]-propionamide as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.90 (s, 1H), 7.92 (s, 1H), 7.05 (s, 1H), 6.90 (s, 1H), 6.70 (m, 3H), 5.90 (s, 2H), 3.59 (d, 2H), 2.94 (t, 2H), 2.57 (s, 3H), 2.40 (t, 2H), 1.28 (s, 6H).

Workup

  1. concentrationthen concentrated

Sources & evidence

ORD record
ord-4a09d69a750a4a42bd682f6cf9086f2c
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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