Hydrochloric Acid → HCID 71657611, compound

HRID 1428672Notes

Reaction equation

HRID 1428672 reaction equation
[C:1]1([CH3:49])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[C:22](C4C=CC(C)=CC=4)=[C:21]([CH2:30][CH2:31][CH2:32][CH2:33][C:34]([NH:36][CH2:37][C:38]([O:40]C)=[O:39])=[O:35])[N:20](C4C=CC(C)=CC=4)[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.[Li+].[OH-].Cl>C1COCC1.O>[C:1]1([CH3:49])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH:22]=[C:21]([CH2:30][CH2:31][CH2:32][CH2:33][C:34]([NH:36][CH2:37][C:38]([OH:40])=[O:39])=[O:35])[NH:20][C:10]3=[N:11][C:12]=2[C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86690322HCID 86690322, compound

Product 1

HCID 71657611HCID 71657611, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(5-(2,3-di-p-tolyldi-p-tolyl-5H-pyrrolo[2,3-b]pyrazin-6-yl)pentanamido)acetate (step 1) (17 mg, 0.036 mmol) in THF (1 ml) and water (0.5 ml) was treated with LiOH. monohydrate (8.12 mg, 0.108 mmol). After stirring at room temperature for 3 hours, the reaction mixture was treated with water (20 ml) and the pH adjusted to pH 2 using 2M HCl. The aqueous portion was extracted with DCM (×3) and the combined organic extracts were concentrated under reduced pressure. Purification by reverse phase (C18) chromatograpy eluting with 0-30% MeCN in water (0.1% TFA) afforded the titled compound;

Workup

  1. extractionThe aqueous portion was extracted with DCM (×3)
  2. concentrationthe combined organic extracts were concentrated under reduced pressure
  3. customPurification by reverse phase (C18) chromatograpy
  4. washeluting with 0-30% MeCN in water (0.1% TFA)

Sources & evidence

ORD record
ord-c0751415528642fc968341bdedb3defa
Source dataset
uspto-grants-2015_01
Patent number
US08937069B2

Reaction notes

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