Ethylenediamine → HCID 178435670, compound

HRID 246543Notes

Reaction equation

HRID 246543 reaction equation
[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N:13][C:14]([C:17]3[C:25]4[C:20](=[C:21]([CH2:26][CH3:27])[CH:22]=[CH:23][CH:24]=4)[NH:19][N:18]=3)=[CH:15][N:16]=[C:11]2[N:10](COCC[Si](C)(C)C)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.C(N)CN>ClCCl.CO.ClCCl>[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N:13][C:14]([C:17]3[C:25]4[C:20](=[C:21]([CH2:26][CH3:27])[CH:22]=[CH:23][CH:24]=4)[NH:19][N:18]=3)=[CH:15][N:16]=[C:11]2[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 178435669N-tert-butyl-2-(7-ethyl-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

Product 1

HCID 178435670HCID 178435670, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of N-tert-butyl-2-(7-ethyl-1H-indazol-3-yl)-5-((2(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (45 mg, 91.3 μmol) in dichloromethane (913 μL) was added trifluoroacetic acid (417 mg, 281 μL, 3.65 mmol) and stirred at room temperature. After 16 h the reaction mixture was concentrated. The residue was dissolved in dichloromethane (913 μL) and ethylenediamine (329 mg, 370 μL, 5.48 mmol) was added and stirred at room temperature. After 1 h the reaction was diluted with 10% methanol/dichloromethane. Purification by chromatography (silica, MeOH/DCM gradient) gave N-tert-butyl-2-(7-ethyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (16 mg, 44.1 μmol, 48%) as a white solid. MS (M+H)+=363.2; 1H NMR (CD3OD) δ: 9.17 (s, 1H), 8.36 (d, J=7.5 Hz, 1H), 8.27 (s, 1H), 7.81 (s, 1H), 7.27 (d, J=7.5 Hz, 1H), 7.18 (t, J=7.5 Hz, 1H), 3.03 (q, J=7.7 Hz, 2H), 1.62 (s, 9H); 1.42 (t, J=7.7 Hz, 3H).

Workup

  1. concentrationAfter 16 h the reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in dichloromethane (913 μL)
  3. stirringstirred at room temperature
  4. customPurification by chromatography (silica, MeOH/DCM gradient)

Sources & evidence

ORD record
ord-bb3c02c3be2845bebeeb590e414574d3
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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