Bis-(1H-imidazol-2-YL)-methanone → HCID 178436415, compound

HRID 2099748Notes

Reaction equation

HRID 2099748 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH:4]([NH2:18])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([CH2:15][CH3:16])[CH:14]=1)[NH:11][N:10]=[C:9]2[CH3:17].[C:20](C1NC=CN=1)(C1NC=CN=1)=[O:21].[NH:32]1[CH2:37][CH2:36][CH:35]([N:38]2[CH2:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[NH:40][C:39]2=[O:48])[CH2:34][CH2:33]1>O1CCCC1>[CH3:1][O:2][C:3](=[O:19])[CH:4]([NH:18][C:20]([N:32]1[CH2:33][CH2:34][CH:35]([N:38]2[CH2:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[NH:40][C:39]2=[O:48])[CH2:36][CH2:37]1)=[O:21])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([CH2:15][CH3:16])[CH:14]=1)[NH:11][N:10]=[C:9]2[CH3:17]

Participants

5

Reactant 3

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 110425973-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneHCID 178436420HCID 178436420, compound

Product 1

HCID 178436415HCID 178436415, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of (±)-2-amino-3-(7-ethyl-3 methyl-1H-indazol-5-yl)-propionic acid methyl ester (0.55 g, 2.1 mmol) in tetrahydrofuran (6 mL) at 0° C. was treated with carbonyl diimidazole (0.37 g, 1.1 equiv). The reaction was stirred for 5 min at 0° C., warmed to room temperature, stirred 10 min, and treated with 3-piperidin-4-yl-3,4-dihydro-1H-quinazolin-2-one (0.53 g, 1.1 equiv). The mixture was stirred at room temperature overnight. The solvent was evaporated and the residue purified by column chromatography to give 0.94 g (86%) as a white powder. 1H-NMR (DMSO-d6) δ 1.26 (t, J=7.5, 3H), 1.49 (m, 1H), 2.44 (s, 3H), 2.83 (dd, J=7.3, 7.6, 1H), 2.84 (dd, J=115.0, 7.6, 1H), 2.88-3.10 (m, 1.5H), 3.18 (d, J=5.5, 0.5H), 3.61 (s, 3H), 4.04-4.16 (m, 3H), 4.28 (m, 2H), 6.76 (d, J=7.9, 1H), 6.86 (m, 2H), 7.04-7.25 (m, 3H), 7.36 (s, 1H), 7.40 (s, 1H), 9.18 (s, 1H), 12.59 (s, 1H). Mass spec.: 519.37 (MH)+.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred 10 min
  3. stirringThe mixture was stirred at room temperature overnight
  4. customThe solvent was evaporated
  5. customthe residue purified by column chromatography
  6. customto give 0.94 g (86%) as a white powder

Sources & evidence

ORD record
ord-e33e4d294df343e2a1add74658da04a9
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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