Water → HCID 86690329, compound

HRID 1521909Notes

Reaction equation

HRID 1521909 reaction equation
[C:1]1([CH3:26])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH:22]=[C:21]([CH2:23][CH2:24][OH:25])[NH:20][C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[C:36](Cl)(=[O:38])[CH3:37].O>C1COCC1>[C:36]([O:25][CH2:24][CH2:23][C:21]1[NH:20][C:10]2=[N:11][C:12]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)=[C:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:26])=[CH:6][CH:5]=3)[N:8]=[C:9]2[CH:22]=1)(=[O:38])[CH3:37]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 86690330HCID 86690330, compound

Product 1

HCID 86690329HCID 86690329, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2,3-Di-p-tolyl-5H-pyrrolo[2,3-b]pyrazin-6-yl)ethanol (step 2) (73 mg, 0.213 mmol) in dry THF (2 ml) at RT was treated with DIPEA (0.082 ml, 0.468 mmol) and acetyl chloride (0.018 ml, 0.255 mmol). After stirring for 16 hours at RT, the mixture was added to water (30 ml) and extracted with DCM (×3). The combined organic extracts were passed through a phase separating column and concentrated under reduced pressure. The crude product was purified by chromatography on silica eluting with 0-40% EtOAc/iso-hexane to afford the title compound, 2-(2,3-dip-tolyl-5H-pyrrolo[2,3-b]pyrazin-6-yl)ethyl acetate;

Workup

  1. extractionextracted with DCM (×3)
  2. customseparating column
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by chromatography on silica eluting with 0-40% EtOAc/iso-hexane

Sources & evidence

ORD record
ord-b722768edb6c41cdaf9ce028c504d678
Source dataset
uspto-grants-2015_07
Patent number
US09073932B2

Reaction notes

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