alpha-Naphthyl isocyanate → HCID 70113234, compound

HRID 2268953Notes

Reaction equation

HRID 2268953 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([N:6]([CH3:22])[C:7]2[N:12]=[C:11]([N:13]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[N:15]=[CH:14]3)[CH:10]=[CH:9][N:8]=2)[CH2:2]1.[C:23]1([N:33]=[C:34]=[O:35])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[C:23]1([NH:33][C:34]([N:1]2[CH2:5][CH2:4][CH:3]([N:6]([CH3:22])[C:7]3[N:12]=[C:11]([N:13]4[C:17]5[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=5[N:15]=[CH:14]4)[CH:10]=[CH:9][N:8]=3)[CH2:2]2)=[O:35])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 66589alpha-Naphthyl isocyanateHCID 18332644HCID 18332644, compound

Product 1

HCID 70113234HCID 70113234, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9.5 mg of 2-[(pyrrolidin-3-yl)-methylamino]-4-[benzimidazol-1-yl]pyrimidine (from EXAMPLE 12, step A) in 1 mL of CH2Cl2 was added 7.1 mg of naphthyl isocyanate. The mixture was stirred at room temperature overnight, then concentrated. The residue was purified by flash chromatography, eluting with a gradient system of 1:1 hexanes-acetone to 1:2 hexanes-acetone, to yield 7.3 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.63 (s, 1H), 8.38 (br s, 1H) 8.19 (d, J=7.8 Hz, 1H), 7.80-7.90 (m, 3H), 7.63 (d, J=8.0 Hz, 1H), 7.35-7.52 (m, 5H), 6.85 (d, J=5.0 Hz, 1H), 6.52 (s, 1H), 3.83 (br t, J=8.2 Hz, 1H), 3.56-3.80 (m, 4H), 3.45 (br t, J=8.0 Hz, 1H), 2.75-2.84 (m, 1H), 2.27 (br s, 1H), 1.62-2.00 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-9363605b74db40a78588e8453510ec83
Source dataset
uspto-grants-2001_12
Patent number
US06329380B1

Reaction notes

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