Sodium Carbonate → Tert-butyl 3-(4-chlorobenzyl)-4-(4-(3-methyl-5-phenyl-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-4-oxobutylcarbamate

HRID 79560Notes

Reaction equation

HRID 79560 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:9]=2[N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[NH:4][CH:3]=1.[C:23]([O:27][C:28]([NH:30][CH2:31][CH2:32][CH:33]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=1)[C:34](O)=[O:35])=[O:29])([CH3:26])([CH3:25])[CH3:24].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>[Cl:44][C:41]1[CH:42]=[CH:43][C:38]([CH2:37][CH:33]([C:34]([N:14]2[CH2:13][CH2:12][N:11]([C:9]3[C:8]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:7][N:6]=[C:5]4[NH:4][CH:3]=[C:2]([CH3:1])[C:10]=34)[CH2:16][CH2:15]2)=[O:35])[CH2:32][CH2:31][NH:30][C:28](=[O:29])[O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:39][CH:40]=1

Participants

8

Reactant 6

HCID 10340Sodium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 687376094-(Tert-butoxycarbonylamino)-2-(4-chlorobenzyl)butanoic acidHCID 687614063-Methyl-5-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 68758679Tert-butyl 3-(4-chlorobenzyl)-4-(4-(3-methyl-5-phenyl-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-4-oxobutylcarbamateYield 12.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methyl-5-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine (0.050 g, 0.137 mmol, see Example 15), 4-(tert-butoxycarbonylamino)-2-(4-chlorobenzyl)butanoic acid (0.0494 g, 0.151 mmol), HOBT-H2O (0.0293 g, 0.192 mmol), and EDCI (0.0341 g, 0.178 mmol) were placed in DCM (3 mL) at room temperature. DIEA (d=0.742; 0.119 mL, 0.684 mmol) was then added, and the reaction was stirred at room temperature for 15 hours. The reaction was then poured into saturated Na2CO3 and extracted with DCM. The combined organic fractions were dried, filtered, concentrated, and purified (500:5 DCM:MeOH) to give tert-butyl 3-(4-chlorobenzyl)-4-(4-(3-methyl-5-phenyl-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)-4-oxobutylcarbamate (0.010 g, 12.1% yield).

Workup

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

Sources & evidence

ORD record
ord-b96e1c83c2d44f9580512575df724249
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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