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

HRID 2250183Notes

Reaction equation

HRID 2250183 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-3,4-dihydro-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-d9009f1c4e644ea2a374550b32c595c1
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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