Ethylenediamine → HCID 71280150, compound

HRID 246460Notes

Reaction equation

HRID 246460 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:17]=[C:16]4[C:18]([C:29]([NH:31][CH:32]([CH2:35][OH:36])[CH2:33][OH:34])=[O:30])=[CH:19][N:20](COCC[Si](C)(C)C)[C:15]4=[N:14][CH:13]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C(N)CN>ClCCl>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:17]=[C:16]4[C:18]([C:29]([NH:31][CH:32]([CH2:33][OH:34])[CH2:35][OH:36])=[O:30])=[CH:19][NH:20][C:15]4=[N:14][CH:13]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 71280553HCID 71280553, compound

Product 1

HCID 71280150HCID 71280150, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-N-(1,3-dihydroxypropan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (0.035 g, 0.066 mmol) in dichloromethane (3 mL) was added TFA (0.38 g, 0.25 mL, 3.3 mmol) at 20° C. After 18 h, the mixture was concentrated in vacuo. The residue was diluted with dichloromethane and concentrated again. The residue was then suspended in dichloromethane (3 mL) and ethylenediamine (0.2 g, 0.22 mL, 3.3 mmol) added. The mixture was stirred for 3 h, then concentrated in vacuo. The residue was collected by filtration and purified by HPLC eluting with MeCN/water (20-95%) to give 2-(6-chloro-1-methyl-1H-indazol-3-yl)-N-(1,3-dihydroxypropan-2-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (0.009 g, 0.022 mmol, 34%) as a white powder. MS (M+H)+=401; 1H NMR (DMSO-d6) δ: 12.86 (br. s., 1H), 9.15 (s, 1H), 8.73 (d, J=8.5 Hz, 1H), 8.44 (s, 1H), 8.24 (d, J=8.8 Hz, 1H), 7.96 (s, 1H), 7.32 (d, J=8.8 Hz, 1H), 4.93-5.02 (m, 2H), 4.17 (s, 4H), 3.56-3.77 (m, 4H).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionThe residue was diluted with dichloromethane
  3. concentrationconcentrated again
  4. concentrationconcentrated in vacuo
  5. filtrationThe residue was collected by filtration
  6. custompurified by HPLC
  7. washeluting with MeCN/water (20-95%)

Sources & evidence

ORD record
ord-caf5bd3a1a2d4c7fa09dbc44b1abec38
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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