Benzoyl isocyanate → HCID 10410099, compound

HRID 1352633Notes

Reaction equation

HRID 1352633 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]1[C:15]2[C:14]([CH3:16])=[C:13]([CH3:17])[N:12]=[C:11]([NH2:18])[C:10]=2[N:9]=[C:8]1[CH2:19][CH3:20].[C:21]([N:29]=[C:30]=[O:31])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[NH2:18][C:11]1[C:10]2[N:9]=[C:8]([CH2:19][CH3:20])[N:7]([CH2:6][CH2:5][O:4][CH2:3][CH2:2][NH:1][C:30]([NH:29][C:21](=[O:28])[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:31])[C:15]=2[C:14]([CH3:16])=[C:13]([CH3:17])[N:12]=1

Participants

3

Reactant 2

HCID 78210Benzoyl isocyanateHCID 21912884HCID 21912884, compound

Product 1

HCID 10410099HCID 10410099, compoundYield 22%

Procedure

A solution of 1-[2-(2-aminoethoxy)ethyl]-2-ethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine (1.60 g, 5.77 mmol) was treated with benzoyl isocyanate (0.98 g, 6.6 mmol) using the method described in Example 105. The crude product was purified by column chromatography on silica gel (150 mL, eluting with 90:10 dichloromethane:methanol) and recrystallized from acetonitrile (75 mL/g). The crystals were subsequently recrystallized twice from 2-propanol (40–44 mL/g) and then stirred in water for 30 minutes and isolated by filtration. The solid was dried for three days under high vacuum to provide 0.54 g of N-{2-[2-(4-amino-2-ethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethoxy]ethyl}-N′-benzoylurea as a white solid, mp 185–187° C. 1HNMR (300 MHz, CDCl3) δ 8.98 (br s, 1H), 8.87 (br t, 1H), 7.93–7.87 (m, 2H), 7.63–7.56 (m, 1H), 7.52–7.44 (m, 2H), 4.84 (s, 2H), 4.45 (t, J=5.8 Hz, 2H), 3.76 (t, J=5.8, 2H), 3.57–3.46 (m, 4H), 2.91 (q, J=7.5, 2H), 2.42 (s, 6H), 1.41 (t, J=7.5, 3H); MS (APCI) m/z 425 (M+H)+; Anal. Calcd for C22H28N6O3.0.25 H2O: C, 61.59; H, 6.70; N, 19.59. Found: C, 61.25; H, 6.90; N, 19.72.

Workup

  1. customThe crude product was purified by column chromatography on silica gel (150 mL, eluting with 90:10 dichloromethane:methanol)
  2. customrecrystallized from acetonitrile (75 mL/g)
  3. customThe crystals were subsequently recrystallized twice from 2-propanol (40–44 mL/g)
  4. customisolated by filtration
  5. customThe solid was dried for three days under high vacuum

Sources & evidence

ORD record
ord-45b2fd728ab34c9495acc808775c3dcc
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

Loading…