Ethylenediamine → HCID 11706580, compound

HRID 551886Notes

Reaction equation

HRID 551886 reaction equation
Cl.C(O[C:5](=[NH:42])[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[C:14]3[N:15]([CH:39]=[CH:40][N:41]=3)[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][C:26](=[O:37])[C:27]4[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=4)[C:20]=3[CH3:38])[N:18]=2)=[CH:8][CH:7]=1)C.[CH2:43](N)[CH2:44][NH2:45]>CO>[C:33]([C:30]1[CH:29]=[CH:28][C:27]([C:26]([NH:25][C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([C:17]3[N:18]=[C:13]([NH:12][C:9]4[CH:8]=[CH:7][C:6]([C:5]5[NH:45][CH2:44][CH2:43][N:42]=5)=[CH:11][CH:10]=4)[C:14]4[N:15]([CH:39]=[CH:40][N:41]=4)[CH:16]=3)[C:20]=2[CH3:38])=[O:37])=[CH:32][CH:31]=1)([CH3:34])([CH3:36])[CH3:35]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 66895115HCID 66895115, compound

Product 1

HCID 11706580HCID 11706580, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

4-{6-[3-(4-tert-Butyl-benzoylamino)-2-methyl-phenyl]-imidazo[1,2-a]pyrazin-8-ylamino}-benzimidic acid ethyl ester hydrochloride (150 mg; 0.26 mmol) is dissolved in methanol (5 mL) in a glass pressure reaction vessel, and ethylenediamine (100 mg; excess) is added. The reaction is heated to 60° C. for 16 hr then concentrated in vacuo. The oil is dissolved in 2 mL CH2Cl2 and diethyl ether (20 mL) is added to precipitate out 4-tert-butyl-N-(3-{8-[4-(4,5-dihydro-1H-imidazol-2-yl)-phenylamino]-imidazo[1,2-a]pyrazin-6-yl}-2-methyl-phenyl)-benzamide as a light tan solid (100 mg). Gradient silica flash chromatography using (90:9:1) (CH2Cl2:methanol:ammonium hydroxide) as the eluent provides the pure material as a white solid (50 mg).

Workup

  1. additionis added
  2. concentrationthen concentrated in vacuo
  3. dissolutionThe oil is dissolved in 2 mL CH2Cl2
  4. additiondiethyl ether (20 mL) is added
  5. customto precipitate out 4-tert-butyl-N-(3-{8-[4-(4,5-dihydro-1H-imidazol-2-yl)-phenylamino]-imidazo[1,2-a]pyrazin-6-yl}-2-methyl-phenyl)-benzamide as a light tan solid (100 mg)

Sources & evidence

ORD record
ord-fb31d4195be54b1ab5a3220adb0565ca
Source dataset
uspto-grants-2011_05
Patent number
US07947835B2

Reaction notes

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