Water → HCID 59754693, compound

HRID 751598Notes

Reaction equation

HRID 751598 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:13]3[N:14]([CH:25]=[CH:26][N:27]=3)[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=3)[N:17]=2)=[CH:7][CH:6]=1)[CH3:2].C(N(CC)CC)C.[C:36]([C:40]1[CH:48]=[CH:47][C:43]([C:44](Cl)=[O:45])=[CH:42][CH:41]=1)([CH3:39])([CH3:38])[CH3:37].O>O1CCCC1>[CH2:1]([O:3][C:4](=[O:28])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:13]3[N:14]([CH:25]=[CH:26][N:27]=3)[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:44](=[O:45])[C:43]4[CH:47]=[CH:48][C:40]([C:36]([CH3:38])([CH3:37])[CH3:39])=[CH:41][CH:42]=4)[CH:19]=3)[N:17]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 743724-tert-Butylbenzoyl chlorideHCID 59754730HCID 59754730, compound

Product 1

HCID 59754693HCID 59754693, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

An ice-cold solution of 4-[6-(3-aminophenyl)imidazo[1,2-a]pyrazin-8-ylamino]benzoic acid ethyl ester (19) (44.2 mmol), triethylamine (66.4 mmol), and tetrahydrofuran (140 mL) is treated dropwise with a solution of 4-t-butylbenzoyl chloride (44.2 mmol) in tetrahydrofuran (60 mL) and the mixture is stirred at room temperature for 1 hr. Water (100 mL) is added and the mixture extracted with ethyl acetate (3×100 mL), the extracts are washed with water (2×100 mL) and brine (1×100 mL), dried over magnesium sulfate and evaporated in vacuo. The residue is triturated with dichloromethane to give 4-{6-[3-(4-tert-butyl-benzoylamino)phenyl]imidazo[1,2-a]pyrazin-8-ylamino}benzoic acid ethyl ester (20) as a pale orange solid.

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×100 mL)
  2. washthe extracts are washed with water (2×100 mL) and brine (1×100 mL)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue is triturated with dichloromethane

Sources & evidence

ORD record
ord-0faee9ea5d3246958ad385acdcda0aa9
Source dataset
uspto-grants-2008_07
Patent number
US07405295B2

Reaction notes

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