Bis-(1H-imidazol-2-YL)-methanone → HCID 24863245, compound

HRID 1353532Notes

Reaction equation

HRID 1353532 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH:4]([NH2:17])[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]=[CH:9]2.[C:19](C1NC=CN=1)(C1NC=CN=1)=[O:20].[NH:31]1[CH2:36][CH2:35][CH:34]([N:37]2[CH2:46][C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[NH:39][C:38]2=[O:47])[CH2:33][CH2:32]1>O1CCCC1>[CH3:1][O:2][C:3](=[O:18])[CH:4]([NH:17][C:19]([N:31]1[CH2:32][CH2:33][CH:34]([N:37]2[CH2:46][C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[NH:39][C:38]2=[O:47])[CH2:35][CH2:36]1)=[O:20])[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]=[CH:9]2

Participants

5

Reactant 3

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 110425973-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneHCID 58864508HCID 58864508, compound

Product 1

HCID 24863245HCID 24863245, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of (±)-2-amino-3-(7-ethyl-1H-indazol-5-yl)-propionic acid methyl ester (100 mg, 0.41 mmol) in tetrahydrofuran (2 mL) at 0° C. was treated with carbonyl diimidazole (66 mg, 1 equiv). The reaction was stirred for 5 min, warmed to room temperature, stirred for 15 min, and then treated with 3-piperidin-4-yl-3,4dihydro-1H-quinazolin-2-one (103 mg, 1.1 equiv). The mixture was stirred at room temperature overnight. The solvent was evaporated and the residue purified by column chromatography to give 188 mg (92%) as a white solid. 1H-NMR (CDCl3, 500 MHz) δ 1.36 (t, J=7.6, 3H), 1.69 (m, 4H), 2.86 (m, 2H), 2.90 (q, J=7.6, 2H), 3.22 (dd, J=5.5, 4.9, 2H), 3.75 (s, 3H), 4.03 (dd, J=44.0, 13.7, 2H), 4.26 (s, 2H), 4.51 (m, 1H), 4.84 (m, 1H), 5.02 (m, 1H), 6.70 (d, J=7.9, 1H), 6.90–7.05 (m, 4H), 7.16 (dd, J=7.6, 7.6, 1H), 7.34 (s, 1H), 8.03 (s, 1H). Mass spec.: 505.29 (MH)+.

Workup

  1. stirringstirred for 15 min
  2. stirringThe mixture was stirred at room temperature overnight
  3. customThe solvent was evaporated
  4. customthe residue purified by column chromatography
  5. customto give 188 mg (92%) as a white solid

Sources & evidence

ORD record
ord-7b7459ba12c648309f63168acd30a051
Source dataset
uspto-grants-2007_05
Patent number
US07220862B2

Reaction notes

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