Sodium Carbonate → HCID 68784056, compound

HRID 79622Notes

Reaction equation

HRID 79622 reaction equation
[C:1]1([C:7]2[C:8]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[C:9]3[C:15]([NH:16][C:17](=[O:24])[C:18]4[CH:23]=[CH:22][CH:21]=[N:20][CH:19]=4)=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:31]([O:35][C:36]([NH:38][CH2:39][CH2:40][C:41](O)=[O:42])=[O:37])([CH3:34])([CH3:33])[CH3:32].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>[C:17]([NH:16][C:15]1[C:9]2[C:10](=[N:11][CH:12]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:8]=2[N:25]2[CH2:26][CH2:27][N:28]([C:41](=[O:42])[CH2:40][CH2:39][NH:38][C:36](=[O:37])[O:35][C:31]([CH3:32])([CH3:33])[CH3:34])[CH2:29][CH2:30]2)[NH:13][CH:14]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[N:20][CH:19]=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 68760217N-(5-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide

Product 1

HCID 68784056HCID 68784056, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(5-Phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (0.050 g, 0.125 mmol, see Example 64), 3-(tert-butoxycarbonylamino)propanoic acid (0.0475 g, 0.251 mmol), HOBT-H2O (0.0269 g, 0.176 mmol), and EDCI (0.0313 g, 0.163 mmol) were placed in DCM (5 mL) at room temperature. DIEA (d 0.742; 0.109 mL, 0.627 mmol) was then added, and the reaction was stirred for 5 hours. The reaction was then poured into Na2CO3 and extracted into DCM. The organic fractions were dried, filtered, and concentrated to give the crude product that was purified by column chromatography (500:20 DCM:MeOH) to give tert-butyl 3-(4-(3-(nicotinamido)-5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-oxopropylcarbamate (0.065 g, 90.9% yield).

Workup

  1. extractionextracted into DCM
  2. customThe organic fractions were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product that
  6. customwas purified by column chromatography (500:20 DCM:MeOH)

Sources & evidence

ORD record
ord-3db005b317f34e2194cfbe4bf21cbc5d
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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