Hydrochloric Acid → HCID 66895115, compound

HRID 551885Notes

Reaction equation

HRID 551885 reaction equation
[C:1]([C:5]1[CH:38]=[CH:37][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[N:19]=[C:20]([NH:27][C:28]4[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=4)[C:21]4[N:22]([CH:24]=[CH:25][N:26]=4)[CH:23]=3)[C:13]=2[CH3:36])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[ClH:39].[CH2:40]([OH:42])[CH3:41]>>[ClH:39].[CH2:40]([O:42][C:34](=[NH:35])[C:31]1[CH:30]=[CH:29][C:28]([NH:27][C:20]2[C:21]3[N:22]([CH:24]=[CH:25][N:26]=3)[CH:23]=[C:18]([C:14]3[CH:15]=[CH:16][CH:17]=[C:12]([NH:11][C:9](=[O:10])[C:8]4[CH:37]=[CH:38][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=4)[C:13]=3[CH3:36])[N:19]=2)=[CH:33][CH:32]=1)[CH3:41]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 66894549HCID 66894549, compound

Product 1

HCID 66895115HCID 66895115, compound

Conditions

Temperature
0 °C

Procedure

4-tert-Butyl-N-{3-[8-(4-cyano-phenylamino)-imidazo[1,2-a]pyrazin-6-yl]-2-methyl-phenyl}-benzamide is slurried in 200 mL ethanol (200 proof) and the reaction cooled to 0° C. in an ice bath. The reaction is then saturated with hydrogen chloride gas and allowed to gradually warm to rt over 16 hrs with stirring. The solvent is removed in vacuo and the resulting tan solid 4-{6-[3-(4-tert-butyl-benzoylamino)-2-methyl-phenyl]-imidazo[1,2-a]pyrazin-8-ylamino}-benzimidic acid ethyl ester hydrochloride (500 mg) is used without further purification.

Workup

  1. temperatureto gradually warm to rt over 16 hrs
  2. customThe solvent is removed in vacuo
  3. customthe resulting tan solid 4-{6-[3-(4-tert-butyl-benzoylamino)-2-methyl-phenyl]-imidazo[1,2-a]pyrazin-8-ylamino}-benzimidic acid ethyl ester hydrochloride (500 mg) is used without further purification

Sources & evidence

ORD record
ord-90a5b1e96dd14206bd32d3a143c108fa
Source dataset
uspto-grants-2011_05
Patent number
US07947835B2

Reaction notes

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