Diisopropylethylamine → N-(1-tert-Butoxycarbonyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1-benzyloxycarbonyl-4-piperidinecarboxamide

HRID 1071346Notes

Reaction equation

HRID 1071346 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:19][CH2:18][CH:14]([C:15](Cl)=[O:16])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]2[N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:28]=[CH:29][C:22]=12.C(N(C(C)C)CC)(C)C>C(#N)C>[C:33]([O:32][C:30]([N:27]1[C:23]2=[N:24][CH:25]=[CH:26][C:21]([NH:20][C:15]([CH:14]3[CH2:18][CH2:19][N:11]([C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:10])[CH2:12][CH2:13]3)=[O:16])=[C:22]2[CH:29]=[CH:28]1)=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2776270Benzyl 4-(chlorocarbonyl)piperidine-1-carboxylateHCID 22393192HCID 22393192, compound

Product 1

HCID 22393147N-(1-tert-Butoxycarbonyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1-benzyloxycarbonyl-4-piperidinecarboxamideYield 102.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Benzyloxycarbonylisonipecotyl chloride (5 g) was added to a solution of 4-amino-1-tert-butoxycarbonyl-1H-pyrrolo[2,3-b]pyridine (3 g) and diisopropylethyamine (2.16 g) in acetonitrile (40 ml) and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice-water and extracted with chloroform. The residue obtained by water washing, drying and then concentration under reduced pressure was purified by silica gel column chromatography to give 6.3 g of N-(1-tert-butoxycarbonyl-1H-pyrrolo-[2,3-b]pyridin-4-yl)-1-benzyloxycarbonyl-4-piperidinecarboxamide.

Workup

  1. extractionextracted with chloroform
  2. customThe residue obtained by water washing
  3. customdrying
  4. concentrationconcentration under reduced pressure
  5. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5cd7f1c4295b4f2d82ee403ff77ec675
Source dataset
uspto-grants-2005_06
Patent number
US06906061B2

Reaction notes

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