Allyl bromide → HCID 67951140, compound

HRID 923646Notes

Reaction equation

HRID 923646 reaction equation
[O:1]=[C:2]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)[CH2:3][N:4]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[S:5]1.[CH2:20](Br)[CH:21]=[CH2:22].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:22]([N:17]1[CH2:18][CH2:19][N:14]([C:2](=[O:1])[CH2:3][N:4]2[C:8](=[O:9])[C:7]3[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=3[S:5]2)[CH2:15][CH2:16]1)[CH:21]=[CH2:20]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 81531DiisopropylethylamineHCID 67813078HCID 67813078, compound

Product 1

HCID 67951140HCID 67951140, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 10 (30 mg, 0.11 mmol) was treated with allyl bromide (16 mg, 0.13 mmol) and DIEA (40 mg, 0.31 mmol) in anhydrous CH2Cl2 (2 mL) at room temperature for 6 h. Allyl bromide then was removed by reduced pressure and the residue was washed by H2O to give the title compound after purification on a thin-layer silica-gel plate (20 cm×20 cm×2 mm) using CH2Cl2/MeOH (9:1) as the developing solution. C16H19N3O2S; white solid; mp 119-120° C.; IR vmax (neat) 3072, 2920, 2857, 2801, 1717, 1653, 1448, 1339, 1262, 1234, 1136, 1038, 1000, 924, 748 cm−1, 1H NMR (400 MHz, CDCl3) δ 8.02 (1H, d, J=8.0 Hz), 7.58 (1H, t, J=7.6 Hz), 7.53 (1H, d, J=8.0 Hz), 7.37 (1H, t, J=7.6 Hz), 5.80 (1H, m), 5.16 (2H, m), 4.69 (2H, s), 3.65 (2H, t, J=5.2 Hz), 3.57 (2H, t, J=5.2 Hz), 2.99 (2H, d, J=6.8 Hz), 2.45 (4H, m); 13C NMR (100 MHz, CDCl3) δ 165.5, 164.7, 134.1, 132.0, 126.7, 125.3, 120.2, 118.5, 61.5, 52.9, 52.5, 45.3, 44.8 (2×), 42.2, 29.8; ESI-HRMS calcd for C16H20N3O2S: 318.1274. found: m/z 318.1274 [M+H]+.

Workup

  1. customAllyl bromide then was removed by reduced pressure
  2. washthe residue was washed by H2O

Sources & evidence

ORD record
ord-6fa0bd477678436c8183cde8199afab9
Source dataset
uspto-grants-2016_03
Patent number
US09278982B2

Reaction notes

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