Sodium Carbonate → HCID 68761488, compound

HRID 79567Notes

Reaction equation

HRID 79567 reaction equation
Cl.Cl.[C:3]1([C:9]2[C:10]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[C:11]3[CH:17]=[CH:16][NH:15][C:12]3=[N:13][CH:14]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:24]([O:28][C:29]([NH:31][CH2:32][CH2:33][C:34](O)=[O:35])=[O:30])([CH3:27])([CH3:26])[CH3:25].C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[O:35]=[C:34]([N:21]1[CH2:20][CH2:19][N:18]([C:10]2[C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[CH:14][N:13]=[C:12]3[NH:15][CH:16]=[CH:17][C:11]=23)[CH2:23][CH2:22]1)[CH2:33][CH2:32][NH:31][C:29](=[O:30])[O:28][C:24]([CH3:26])([CH3:25])[CH3:27]

Participants

8

Reactant 6

HCID 10340Sodium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 687587805-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine dihydrochloride

Product 1

HCID 68761488HCID 68761488, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyri dine dihydrochloride (0.10 g, 0.285 mmol, see Example 19), 3-(tert-butoxycarbonylamino)propanoic acid (0.0646 g, 0.342 mmol), HOBT-H2O (0.0610 g, 0.399 mmol), and EDCI (0.0709 g, 0.370 mmol) were placed in DCM (5 mL) at room temperature. DIEA (d 0.742; 0.248 mL, 1.42 mmol) was then added, and the reaction was stirred at room temperature for 18 hours. The reaction was then poured into Na2CO3 and extracted with DCM. The combined organic fractions were dried, filtered, concentrated and purified (500:10 DCM:MeOH) to give tert-butyl 3-oxo-3-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propylcarbamate (0.055 g, 43.0% yield).

Workup

  1. extractionextracted with DCM
  2. customThe combined organic fractions were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified (500:10 DCM:MeOH)

Sources & evidence

ORD record
ord-43dd75321c944660a715c46eb82c9e26
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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