Acetic Anhydride → HCID 68758316, compound

HRID 79599Notes

Reaction equation

HRID 79599 reaction equation
Cl[C:2]1[CH:7]=C[C:5]([C@@H:8](CNC(C)C)[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]4[NH:23][CH:24]=[C:25]([NH:26]C(=O)CCC)[C:18]=34)[CH2:13][CH2:12]2)=O)=[CH:4][CH:3]=1.C(O[C:41](=[O:43])[CH3:42])(=O)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.N1C=CC=CC=1.CO.[Li+].[OH-]>[CH2:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]3[NH:23][CH:24]=[C:25]([NH:26][C:41](=[O:43])[CH3:42])[C:18]=23)[CH2:13][CH2:12]1)[C:8]1[CH:7]=[CH:2][CH:3]=[CH:4][CH:5]=1

Participants

8

Reactant 3

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 44199250(S)-N-(4-(4-(2-(4-chlorophenyl)-3-(isopropylamino)propanoyl)piperazin-1-yl)-1H-pyrrolo [2,3-b]pyridin-3-yl)butyramide

Product 1

HCID 68758316HCID 68758316, compoundYield 88%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 3939Lithium HydroxideSolventHCID 6344DichloromethaneSolvent

Procedure

4-(4-Benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-amine (0.35 g, 1.14 mmol, see Example 25) was placed in DCM (2 mL) and pyridine (1 mL). Acetic anhydride (0.129 mL, 1.37 mmol) was then added, and the reaction was stirred at room temperature for 1 hour. The reaction was then diluted with MeOH (5 mL), and 3M LiOH (0.5 mL) was added. The reaction was stirred for 10 minutes and then poured into saturated Na2CO3 and extracted into DCM. The organic fractions were combined, dried, filtered and concentrated to give a crude residue that was purified by column chromatography (500:8-500:20 DCM:MeOH) to give N-(4-(4-benzylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetamide (0.35 g, 88.0% yield).

Workup

  1. additionwas added
  2. stirringThe reaction was stirred for 10 minutes
  3. extractionextracted into DCM
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude residue that
  8. customwas purified by column chromatography (500:8-500:20 DCM:MeOH)

Sources & evidence

ORD record
ord-6d055f8f49ec4b51a6bd66b85fe8eb49
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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