Phenyl isocyanate → HCID 18332643, compound

HRID 2268954Notes

Reaction equation

HRID 2268954 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:30]=[C:31]=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1>[C:24]1([NH:30][C:31]([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:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanate2×HCID 18332638HCID 18332638, compound

Product 1

HCID 18332643HCID 18332643, compoundYield 57.7%

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 7.6 mg of phenyl isocyanate. The mixture was stirred at room temperature overnight. An additional 7.6 mg of phenyl isocyanate was added and the mixture was stirred for an additional 24 h, then concentrated. The residue was purified by flash chromatography, eluting with 1:1 hexanes-acetone, to yield 12 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.61 (s, 1H), 8.37 (d, J=5.3, 1H) 8.17 (d, J=7.3 Hz, 1H), 7.36-7.44 (m, 2H), 7.22-7.34 (m, 3H), 7.00 (t, J=7.3 Hz, 1H), 6.78 (d, J=5.3 Hz, 1H), 6.52 (s, 1H), 5.75 (br s, 1H), 3.97 (dd, J=3.4, 13.0 Hz, 1H), 3.77 (dt, J=4.4, 13.0 Hz, 1H), 3.41-3.57 (m, 2H), 3.14 (br t, J=10.5 Hz, 1H), 3.02 (dd, J=8.9, 13.3 Hz, 1H), 1.92-2.08(m, 2H), 1.72-1.84 (m, 1H), 1.53-1.64 (m, 1H), 1.41 (ddt, J=3.9, 9.8, 10.1 Hz, 1H). Mass spectrum (EST) 428.2 (M+1).

Workup

  1. stirringthe mixture was stirred for an additional 24 h
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography
  4. washeluting with 1:1 hexanes-acetone

Sources & evidence

ORD record
ord-899ab75bfa0d49fb909846527085cef0
Source dataset
uspto-grants-2001_12
Patent number
US06329380B1

Reaction notes

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