Methyl Isocyanate → HCID 19921641, compound

HRID 1463358Notes

Reaction equation

HRID 1463358 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([OH:27])[CH:25]=4)[NH:20][CH:19]=3)[CH2:11][CH2:10]2)=[N:5][CH:6]=[N:7][CH:8]=1.[CH3:28][N:29]=[C:30]=[O:31]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([O:27][C:30](=[O:31])[NH:29][CH3:28])[CH:25]=4)[NH:20][CH:19]=3)[CH2:11][CH2:10]2)=[N:5][CH:6]=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 15288320HCID 15288320, compound

Product 1

HCID 19921641HCID 19921641, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[3-[4-(5-methoxy-4-pyrimidinyl)-1-piperazinyl]propyl]-5-hydroxyindole (0.170 g, 0.46 mmol) in 6 mL of CH2Cl2 was added methyl isocyanate (60 μL, 1.0 mmol) and the mixture was stirred at room temperature for 4 days. The mixture was then evaporated and the resulting pinkish-gray foam was triturated with isopropanol-ether to give a light grey solid. This material was chromatographed (SiO2 /EtOAc-MeOH, 95:5; then 90:10) to give the title compound (0.120 g, 60%) as a light gray solid, m.p. 120°-122° C. IR (KBr) 3400, 3220, 1730 cm-1 ; 1H NMR (CDCl3, 200 MHz) δ8.33 (s, 1H), 8.06 (br s, 1H), 7.88 (s, 1H), 7.34-7.26 (m, 2H), 6.99-6.91 (m, 2H), 5.00 (br m, 1H), 3.85 (s, 3H), 3.79 (t, J=4.7 Hz, 4H), 2.91 (d, J=4.8 Hz, 3H), 2.75 (t, J=7.4 Hz, 2H), 2.54 (t, J=4.8 Hz, 4H), 2.45 (t, J=7.6 Hz, 2H), 2.04-1.83 (m, 2 H) Anal. Calcd. for C22H28N6O3 0.8H2O: C, 60.20; H, 6.80; N, 19.15. Found: C, 60.13; H, 6.40; N, 18.75.

Workup

  1. customThe mixture was then evaporated
  2. customthe resulting pinkish-gray foam was triturated with isopropanol-ether
  3. customto give a light grey solid
  4. customThis material was chromatographed (SiO2 /EtOAc-MeOH, 95:5

Sources & evidence

ORD record
ord-82f00e9f8bd4414c82cc886369cf0306
Source dataset
uspto-grants-1994_04
Patent number
US05300506

Reaction notes

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