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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Tert-butyl[2-[n-[1-(1h-pyrrolo[2,3-c]pyridin-2-yl)ethyl]carbamoyl]ethyl]carbamate

HRID 1821878
Notes
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Reaction equation

HRID 1821878 reaction equation
Cl.Cl.[NH:3]1[C:7]2=[CH:8][N:9]=[CH:10][CH:11]=[C:6]2[CH:5]=[C:4]1[CH:12]([NH2:14])[CH3:13].[C:15]([NH:22][CH2:23][CH2:24][C:25](O)=[O:26])([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(N(C(C)C)CC)(C)C.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[C:18]([O:17][C:15](=[O:16])[NH:22][CH2:23][CH2:24][C:25](=[O:26])[NH:14][CH:12]([C:4]1[NH:3][C:7]2=[CH:8][N:9]=[CH:10][CH:11]=[C:6]2[CH:5]=1)[CH3:13])([CH3:21])([CH3:19])[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 81531DiisopropylethylamineHCID 689820051h-Pyrrolo[2,3-c]pyridine-2-methanamine,a-methyl-,dihydrochloride

Product 1

HCID 57893518
Tert-butyl[2-[n-[1-(1h-pyrrolo[2,3-c]pyridin-2-yl)ethyl]carbamoyl]ethyl]carbamate
Yield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethylamine dihydrochloride (Example 75) (108 mg, 0.46 mmol), N-Boc-β-alanine (71 mg, 0.37 mmol), diisopropylethylamine (0.31 mL, 1.85 mmol), EDCI (78 mg, 0.41 mmol) and HOBt (catalytic amount) in methylene chloride (2.2 mL) was stirred at room temperature under a nitrogen atmosphere overnight (22 h). The reaction mixture was concentrated to dryness under reduced pressure. The residue was dissolved in CH2Cl2, washed with water and saturated NaHCO3, and dried over Na2SO4. Filtration and concentration provided tert-butyl[2-[N-[1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethyl]carbamoyl]ethyl]carbamate (70 mg, 58%) as a tan solid: 1H NMR (500 MHz, CD3OD) δ1.45 (9H, s), 1.63 (3H, d), 2.37-2.51 (2H, m), 3.30-3.42 (2H, m), 5.26-5.35 (1H, m), 6.43 (1H, s), 7.48-7.51 (1H, m), 7.99-8.05 (1H, m), 8.60 (1H, s); ESI MS m/z 333 [C17H24N4O3+H]+; HPLC (Method A) 95.9% (AUC), tR=14.39 min.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washwashed with water and saturated NaHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-2b37d128947c48f39067a318dac00bee
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07608627B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes