Sodium Carbonate → HCID 68764850, compound

HRID 79617Notes

Reaction equation

HRID 79617 reaction equation
N[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:16]([Br:17])=[CH:15][N:14]=[C:13]3[NH:18][CH:19]=[C:20]([NH:21][C:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=4)[C:12]=23)[CH2:7][CH2:6]1)=[O:4].[C:30]([O:34][C:35]([NH:37][CH2:38]CC(O)=O)=[O:36])([CH3:33])([CH3:32])[CH3:31].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>[Br:17][C:16]1[C:11]([N:8]2[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH2:2][CH2:38][NH:37][C:35](=[O:36])[O:34][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:6][CH2:7]2)=[C:12]2[C:20]([NH:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=3)=[CH:19][NH:18][C:13]2=[N:14][CH:15]=1

Participants

8

Reactant 6

HCID 10340Sodium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 44198123HCID 44198123, compound

Product 1

HCID 68764850HCID 68764850, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude N-(5-bromo-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (0.200 g, 0.498 mmol, see Example 61), 3-(tert-butoxycarbonylamino)propanoic acid (0.189 g, 0.997 mmol), HOBT-H2O (0.107 g, 0.698 mmol) and EDCI (0.124 g, 0.648 mmol) were placed in DCM (5 mL) at room temperature. DIEA (d 0.742; 0.434 mL, 2.49 mmol) was then added, and the reaction was allowed to stir for 5 hours. The reaction was then poured into saturated Na2CO3 and extracted into DCM. The organic fractions were combined, dried, filtered, and concentrated to give the crude residue. Purification by column chromatography (500:15 to 500:25 D CM: MeOH) gave tert-butyl 3-(4-(5-bromo-3-(nicotinamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-oxopropylcarbamate (0.060 g, 21.0% yield).

Workup

  1. extractionextracted into DCM
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude residue
  6. customPurification by column chromatography (500:15 to 500:25 D CM: MeOH)

Sources & evidence

ORD record
ord-1a3a58eb737b459283e6a3a8fb0fa93c
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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