Trimethylsilyl isocyanate → HCID 58996971, compound

HRID 251209Notes

Reaction equation

HRID 251209 reaction equation
[CH3:1][C:2]1[C:3]([CH2:9][N:10]([CH:15]2[C:24]3[N:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH2:18][CH2:17][CH2:16]2)[CH2:11][CH2:12][CH2:13][NH2:14])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.C[Si]([N:29]=[C:30]=[O:31])(C)C>CC(O)C>[CH3:1][C:2]1[C:3]([CH2:9][N:10]([CH:15]2[C:24]3[N:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH2:18][CH2:17][CH2:16]2)[CH2:11][CH2:12][CH2:13][NH:14][C:30]([NH2:29])=[O:31])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 68960977HCID 68960977, compound

Product 1

HCID 58996971HCID 58996971, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of N1-(3,5-Dimethyl-pyridin-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-propane-1,3-diamine (101 mg, 0.31 mmol) in 2-propanol (4 mL) was added trimethylsilyl-isocyanate (65 μL, 0.48 mmol). The resultant solution was stirred at room temperature overnight then concentrated. Purification of the crude material by radial chromatography on silica gel (1 mm plate, 20:1:1 CH2Cl2-MeOH—NH4OH) provided 83 mg (73%) of the free base of the title compound as a white foam. Conversion of the white foam to the HBr salt gave COMPOUND 363 as a white solid. 1H NMR (D2O) δ 1.40-1.50 (m, 2H), 1.71-1.84 (m, 1H), 1.99-2.23 (m, 2H), 2.34-2.40 (m, 2H), 2.41 (s, 3H), 2.44 (s, 3H), 2.63-2.73 (m, 1H), 2.88 (t, 2H, J=6.3 Hz), 2.95-2.98 (m, 2H), 4.12 (d, 1H, J=17.4 Hz), 4.33 (d, 1H, J=17.4 Hz), 4.45 (dd, 1H, J=5.7, 10.5 Hz), 7.83 (dd, 1H, J=7.8, 5.4 Hz), 8.18 (s, 1H), 8.32 (d, 1H, J=7.8 Hz), 8.42 (s, 1H), 8.57 (d, 1H, J=5.4 Hz); 13C NMR (D2O) δ 17.06, 17.52, 20.46, 20.62, 27.83, 28.80, 37.85, 49.55, 51.95, 61.05, 125.86, 136.65, 137.41, 137.78, 139.38, 140.73, 148.09, 148.74, 149.24, 151.20; ES-MS m/z 368 (M+H). Anal. Calcd. For C21H29N5O.3.0HBr.2.9H2O: C, 38.07; H, 5.75; N, 10.57; Br, 36.18. Found: C, 38.05; H, 5.86; N, 10.68; Br, 36.20.

Workup

  1. concentrationthen concentrated
  2. customPurification of the crude material by radial chromatography on silica gel (1 mm plate, 20:1:1 CH2Cl2-MeOH—NH4OH)

Sources & evidence

ORD record
ord-cc14078cf6cb4c75871e715229850688
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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