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Bis-(1H-imidazol-2-YL)-methanone → HCID 11307630, compound

HRID 2099809
Notes
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Reaction equation

HRID 2099809 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][CH:12]([C:14]2[N:18]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[N:17]=[N:16][N:15]=2)[NH2:13])[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.[C:24](C1NC=CN=1)(C1NC=CN=1)=[O:25].[NH:36]1[CH2:41][CH2:40][CH:39]([N:42]2[CH2:51][C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[NH:44][C:43]2=[O:52])[CH2:38][CH2:37]1>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][CH:12]([NH:13][C:24]([N:36]2[CH2:37][CH2:38][CH:39]([N:42]3[CH2:51][C:50]4[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=4)[NH:44][C:43]3=[O:52])[CH2:40][CH2:41]2)=[O:25])[C:14]2[N:18]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[N:17]=[N:16][N:15]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 110425973-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneHCID 57794577HCID 57794577, compound

Product 1

HCID 11307630HCID 11307630, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 2-(7-methyl-1H-indazol-5-yl)-1-(1-neopentyl-1H-tetrazol-5-yl)ethanamine (20.0 mg, 0.06 mmol) in dimethylformamide (1.0 mL) at 0° C. was treated with carbonyl diimidazole (11.0 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 3-(piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one (15.0 mg, 1.1 equiv). The mixture was stirred at room temperature overnight. The solvent was evaporated and the residue purified by column chromatography to afford 22.0 mg (64%). 1H-NMR (CD3OD, 500 MHz) δ 0.90 (s, 9H), 1.35-1.60 (m, 4H), 2.53 (s, 3H), 2.71-2.85 (m, 2H), 3.41-3.52 (m, 2H), 3.98-4.14 (m, 5H), 4.24 (d, J=14.3, 1H), 4.34 (m, 1H), 6.77 (d, J=7.9, 1H), 6.94 (dd, J=7.6, 7.3, 1H), 7.06-7.17 (m, 3H), 7.45 (s, 1H), 7.88 (s, 1H), 7.98 (s, 1H). Mass spec.: 571.28 (MH)+.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 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 afford 22.0 mg (64%)

Sources & evidence

ORD record
ord-caaa184569df4cb085fb6c50351d353e
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07569578B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes