Water → HCID 71279939, compound

HRID 246086Notes

Reaction equation

HRID 246086 reaction equation
[CH:1]([NH:4][C:5]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([C:16]3[C:24]4[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=4)[N:18]([CH3:26])[N:17]=3)[N:14]=2)[N:9](COCC[Si](C)(C)C)[CH:8]=1)=[O:6])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.C(N)CN.O>ClCCl.C(OCC)(=O)C>[CH:1]([NH:4][C:5]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([C:16]3[C:24]4[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=4)[N:18]([CH3:26])[N:17]=3)[N:14]=2)[NH:9][CH:8]=1)=[O:6])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 71280260HCID 71280260, compound

Product 1

HCID 71279939HCID 71279939, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(6-Chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide (45 mg, 0.09 mmol) was dissolved in dichloromethane (0.9 ml) and cooled in ice bath. Trifluoroacetic acid (0.3 ml) was added slowly and the reaction was stirred at room temperature for 3.5 h. The reaction was evaporated and the residue was dissolved in dichloromethane (2 ml). Ethylenediamine (0.36 ml, 5.4 mmol) was added and the mixture was stirred at room temperature for 18 h. Water and then ethyl acetate were added to the mixture. The resulting precipitate was filtered off, rinsed with water and dried under high vacuum to give 21 mg (81%) of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide. (M+Na)+=391; mp=356-362° C. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.79-12.90 (m, 1H) 9.09 (s, 1H) 8.44 (d, J=9.1 Hz, 1H) 8.42 (s, 1H) 8.02 (d, J=7.6 Hz, 1H) 8.00 (d, J=1.5 Hz, 1H) 7.30 (dd, J=8.8, 1.8 Hz, 1H) 4.19-4.27 (m, 1H) 4.17 (s, 3H) 1.32 (d, J=6.6 Hz, 6H).

Workup

  1. temperaturecooled in ice bath
  2. customThe reaction was evaporated
  3. dissolutionthe residue was dissolved in dichloromethane (2 ml)
  4. stirringthe mixture was stirred at room temperature for 18 h
  5. filtrationThe resulting precipitate was filtered off
  6. washrinsed with water
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-6267b94204714eb8b24f40a7d7c1f85a
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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