alpha-Naphthyl isocyanate → HCID 70138068, compound

HRID 2268955Notes

Reaction equation

HRID 2268955 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([N:7]([CH3:23])[C:8]2[N:13]=[C:12]([N:14]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[N:16]=[CH:15]3)[CH:11]=[CH:10][N:9]=2)[CH2:2]1.[C:24]1([N:34]=[C:35]=[O:36])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1>C1COCC1>[C:24]1([NH:34][C:35]([N:1]2[CH2:6][CH2:5][CH2:4][CH:3]([N:7]([CH3:23])[C:8]3[N:13]=[C:12]([N:14]4[C:18]5[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=5[N:16]=[CH:15]4)[CH:11]=[CH:10][N:9]=3)[CH2:2]2)=[O:36])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 66589alpha-Naphthyl isocyanateHCID 18332638HCID 18332638, compound

Product 1

HCID 70138068HCID 70138068, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 15 mg of 2-[(piperidin-3-yl)-methylamino]-4-[benzimidazol-1-yl]pyrimidine (from EXAMPLE 6) in 2 mL of THF was added 11 mg of naphthyl isocyanate. The mixture was stirred at room temperature for 2 days, then concentrated. The residue was purified by flash chromatography, eluting with a gradient system of 2:1 CH2Cl2-acetone to 1:1 CH2Cl2-acetone, to yield 12 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.56 (s, 1H), 8.25 (br s, 1H) 8.14 (d, J=8.0 Hz, 6.69 (d, J=5.3 Hz, 1H), 4.04 (br s, 1H), 3.85 (br d, J=1.7 Hz, 1H), 3.40-3.55 (m, 2H), 3.12 (br s, 1H), 3.05 (br t, J=9.6 Hz, 1H), 2.36 (br s, 1H), 1.90-2.10 (m, 2H), 1.74-1.85 (m, 1H), 1.56-1.68 (m, 1H), 1.42 (ddt, J=3.9, 10.1, 10.1 Hz, 1H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography
  3. washeluting with a gradient system of 2:1 CH2Cl2-acetone to 1:1 CH2Cl2-acetone

Sources & evidence

ORD record
ord-a424807d7c8848a98d1c6652b686fda4
Source dataset
uspto-grants-2001_12
Patent number
US06329380B1

Reaction notes

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