Diisopropylethylamine → HCID 68760219, compound

HRID 79604Notes

Reaction equation

HRID 79604 reaction equation
C([O:8][CH2:9][C:10]([NH:12][C:13]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][C:20]=2[N:22]2[CH2:27][CH2:26][N:25](CC3C=CC=CC=3)[CH2:24][CH2:23]2)[NH:15][CH:14]=1)=[O:11])C1C=CC=CC=1.CCN(C(C)C)C(C)C>CO.Cl.[Pd]>[OH:8][CH2:9][C:10]([NH:12][C:13]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][C:20]=2[N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[NH:15][CH:14]=1)=[O:11]

Participants

6

Reactant 2

HCID 81531DiisopropylethylamineHCID 687601872-(benzyloxy)-N-(4-(4-benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetamide

Product 1

HCID 68760219HCID 68760219, compoundYield 99.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

2-(Benzyloxy)-N-(4-(4-benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetamide (0.100 g, 0.219 mmol) was placed in MeOH (2 mL). Pd/C (0.0467 g, 0.0220 mmol) was then added, followed by the addition of 3 drops of concentrated HCl. The reaction was next placed under an H2 filled balloon for 3 hours. Additional Pd/C (0.0467 g, 0.0219 mmol) was then added, and the reaction was placed under an H2 filled balloon for an additional 3 hours to drive the reaction to completion. DIEA was added to achieve solubility. The reaction was then filtered, washed with MeOH, and concentrated to give the crude product 2-hydroxy-N-(4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetamide (0.060 g, 99.2% yield).

Workup

  1. customfor 3 hours
  2. customfor an additional 3 hours
  3. customthe reaction to completion
  4. filtrationThe reaction was then filtered
  5. washwashed with MeOH
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f1436fad342247f695d902acc6d3ac9c
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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