Methyl Isocyanate → 2-[1-(1-(N-Methylcarbamoyl)piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine

HRID 2268965Notes

Reaction equation

HRID 2268965 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH2:2]1.[CH3:25][N:26]=[C:27]=[O:28]>C(Cl)Cl>[CH3:25][NH:26][C:27]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH2:2]1)=[O:28]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 183326302-[1-(Piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine

Product 1

HCID 183326672-[1-(1-(N-Methylcarbamoyl)piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[1-(piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine (EXAMPLE 18) (51 mg, 0.16 mmol) in CH2Cl2 (1.6 mL) was added methylisocyanate (10.5 lL, 0.176 mmol) at room temperature. After the reaction was complete (2-3 h), the solvent was removed under reduced pressure, and the crude product was purified by preparative thin layer chromatography (4:1 acetone:hexane system as an eluent) to obtain the title compound. Partial 1H NMR (500 MHz, CDCl3): δ 8.61 (s, 1H); 8.36 (d, J=5.0 Hz, 1H); 8.16 (d, J=7.6 Hz, 1H); 7.85 (d, J=7.1 Hz, 1H); 7.38 (m, 2H); 6.78 (d, J=5.5 Hz, 1H); 4.17 (m, 1H); 4.07 (d, J=11 Hz, 1H); 3.76 (d, J=12.6 Hz, 1H); 2.78 (d, J=4.6 Hz, 3H); 1.31 (d, J=6.6 Hz, 3H). Mass spectrum 380.3 (ESI, M+1).

Workup

  1. custom(2-3 h)
  2. customthe solvent was removed under reduced pressure
  3. customthe crude product was purified by preparative thin layer chromatography (4:1 acetone

Sources & evidence

ORD record
ord-8448eb877f7640059c372733e2571675
Source dataset
uspto-grants-2001_12
Patent number
US06329380B1

Reaction notes

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