Trimethylsilyl isocyanate → HCID 58997037, compound

HRID 1592469Notes

Reaction equation

HRID 1592469 reaction equation
[CH3:1][C:2]1[C:3]([CH2:8][N:9]([CH2:14][C:15]2[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:11][CH2:12][NH2:13])=[N:4][CH:5]=[CH:6][CH:7]=1.C[Si]([N:26]=[C:27]=[O:28])(C)C>CC(O)C>[CH3:1][C:2]1[C:3]([CH2:8][N:9]([CH2:14][C:15]2[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:11][CH2:12][NH:13][C:27]([NH2:26])=[O:28])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 67271094HCID 67271094, compound

Product 1

HCID 58997037HCID 58997037, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The amine from above was dissolved in i-PrOH (3 mL) and treated with trimethylsilylisocyanate (93 μL, 0.69 mmol) at room temperature for 16 hours. The solution was then concentrated under reduced pressure and dried in vacuo. The crude material was then purified by column chromatography with silica gel (20:1:0.1 CH2Cl2/MeOH/NH4OH) to give {3-[Bis-(3-methyl-pyridin-2-ylmethyl)-amino]-propyl}-urea as a colorless oil (82 mg, 51% 2 steps). 1H NMR (CDCl3) δ 1.67 (m, 2H), 2.22 (s, 6H), 2.67 (t, 2H, J=7.5 Hz), 3.10 (m, 2H), 3.69 (s, 4H), 4.78 (br, 2H(NH2)), 7.10 (m, 2H), 7.42 (d, 2H, J=6.0 Hz), 8.36 (d, 2H, J=2.8 Hz). Conversion to the HBr salt gave COMPOUND 179 as a white solid. 1H NMR (D2O) δ 1.66 (m, 2H), 2.51 (s, 6H), 2.68 (m, 2H), 2.99 (t, 2H, J=6.5 Hz), 4.32 (s, 4H), 7.87 (t, 2H, J=6.9 Hz), 8.38 (d, 2H, J=7.8 Hz), 8.61 (d, 1H, J=5.4 Hz). 13C NMR (D2O) δ 17.25 (2C), 26.16, 37.79, 52.47, 54.30 (2C), 126.06 (2C), 137.83 (2C), 138.72 (2C), 148.54 (2C), 150.98 (2C), 161.74. ES-MS m/z 328 (M+H). Anal. Calcd. for C18H25N5093.0HBr.2.7H2O: C, 34.94; H, 5.44; N, 11.32; Br, 38.74. Found: C, 34.99; H, 5.34; N, 10.92; Br, 38.86.

Workup

  1. concentrationThe solution was then concentrated under reduced pressure
  2. customdried in vacuo
  3. customThe crude material was then purified by column chromatography with silica gel (20:1:0.1 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-c193b09d1c2f492ea372e20413279488
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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