Trimethylsilyl isocyanate → HCID 59694160, compound

HRID 899715Notes

Reaction equation

HRID 899715 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[CH:12]1[C:21]2[N:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:15][CH2:14][CH2:13]1.C[Si]([N:32]=[C:33]=[O:34])(C)C>C(O)(C)C>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([CH:12]1[C:21]2[N:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:15][CH2:14][CH2:13]1)[CH:22]1[CH2:27][CH2:26][N:25]([C:33]([NH2:32])=[O:34])[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 10126165HCID 10126165, compound

Product 1

HCID 59694160HCID 59694160, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of (1H-benzimidazol-2-ylmethyl)-piperidin-4-yl-(5,6,7,8-tetrahydroquinolin-8-yl)-amine (0.16 g, 0.43 mmol) in isopropanol (3 mL) was treated with trimethylsilylisocyanate (81 μL, 0.60 mmol) at room temperature. The reaction was stirred 20 hours and concentrated under reduced pressure. This afforded, after column chromatography with silica gel (5:0.5:94.5 MeOH:NH4OH:CH2Cl2), 4-[(1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydroquinolin-8-yl)-amino]-piperidine-1-carboxylic acid amide (112 mg, 66%). 1H NMR (CDCl3) δ 1.42 (m, 1H), 1.60-1.95 (m, 5H), 2.02 (br, 1H), 2.24 (br, 1H), 2.60-2.80 (m, 4H), 2.89 (m, 1H), 3.70 (br, 1H), 4.03 (br, 1H), 4.15 (m, 3H), 4.39 (br, 2H, NH2), 7.18 (m, 3H), 7.45 (d, 1H, J=7.5 Hz), 7.66 (br, 2H), 8.59 (d, 1H, J=4.0 Hz).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-69e52c2b1bd74a4fa78c819900e1626a
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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