Bis-(1H-imidazol-2-YL)-methanone → HCID 11444467, compound

HRID 2099805Notes

Reaction equation

HRID 2099805 reaction equation
[N:1]1[N:2]=[C:3]([CH:10]([NH2:22])[CH2:11][C:12]2[CH:13]=[C:14]3[C:18](=[C:19]([CH3:21])[CH:20]=2)[NH:17][N:16]=[CH:15]3)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[C:23](C1NC=CN=1)(C1NC=CN=1)=[O:24].[F:35][C:36]1[CH:37]=[CH:38][CH:39]=[C:40]2[C:45]=1[NH:44][C:43](=[O:46])[N:42]([CH:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1)[CH2:41]2>CN(C)C=O>[N:1]1[N:2]=[C:3]([CH:10]([NH:22][C:23]([N:50]2[CH2:51][CH2:52][CH:47]([N:42]3[CH2:41][C:40]4[C:45](=[C:36]([F:35])[CH:37]=[CH:38][CH:39]=4)[NH:44][C:43]3=[O:46])[CH2:48][CH2:49]2)=[O:24])[CH2:11][C:12]2[CH:13]=[C:14]3[C:18](=[C:19]([CH3:21])[CH:20]=2)[NH:17][N:16]=[CH:15]3)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 211022172(1h)-Quinazolinone,8-fluoro-3,4-dihydro-3-(4-piperidinyl)-HCID 57794665HCID 57794665, compound

Product 1

HCID 11444467HCID 11444467, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 1-([1,2,4]triazolo[4,3-a]pyridine-3-yl)-2-(7-methyl-1H-indazol-5-yl)ethanamine (30 mg, 0.1 mmol) in dimethylformamide (1.0 mL) at 0° C. was treated with carbonyl diimidazole (17.5 mg, 1.1 equiv). The reaction was stirred for 5 min at 0° C., warmed to room temperature, stirred for 10 min, and treated with 8-fluoro-3-(piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one (26.0 mg, 1.1 equiv). The mixture was then stirred at room temperature overnight. The solvent was evaporated and the residue purified by column chromatography to afford 30 mg (53%). 1H-NMR (CD3OD, 300 MHz) δ 1.25-1.60 (m, 5H), 2.50 (s, 3H), 2.67-2.81 (m, 2H), 3.60 (s, 1H), 3.62 (s, 1H), 3.12-4.18 (m, 4H), 4.25-4.45 (m, 1H), 5.80 (dd, J=8.1, 8.1, 1H), 6.08-7.04 (m, 4H), 7.10 (s, 1H), 7.35-7.44 (s, 1H), 7.49 (s, 1H), 7.70 (m, 1H), 7.96 (s, 1H), 8.41 (d, J=7.0, 1H). Mass spec.: 568.10 (MH)+.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 10 min
  3. stirringThe mixture was then stirred at room temperature overnight
  4. customThe solvent was evaporated
  5. customthe residue purified by column chromatography
  6. customto afford 30 mg (53%)

Sources & evidence

ORD record
ord-fa11c24d74c64227b47367f469a1d2a4
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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