Methanol → HCID 73295271, compound

HRID 522947Notes

Reaction equation

HRID 522947 reaction equation
[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=3)[N:15]=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.CO.[OH-].[NH4+]>ClCCl>[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 131735546HCID 131735546, compound

Product 1

HCID 73295271HCID 73295271, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-tert-butyl-2-(5-methylpyridin-2-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (162 mg, 356 μmol) in dichloromethane (3 mL) was added trifluoroacetic acid (813 mg, 549 μL, 7.13 mmol) and the mixture stirred at room temperature for 16 h. The mixture was then concentrated in vacuo and the residue obtained was dissolved in dichloromethane (3 mL), methanol (1 mL) and ammonium hydroxide (0.6 mL) and the mixture stirred at room temperature for 30 min. The yellow precipitate formed was collected by filtration and dried. The mother liquor was purified by chromatography (silica, 5-25% of a 1:4 methanol:dichloromethane solution in dichloromethane) and combined with the solid to give N-tert-butyl-2-(5-methylpyridin-2-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (77 mg, 237 μmol, 67%) as an off-white solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.37 (s, 1H), 9.88 (s, 1H), 8.38 (s, 1H), 8.13 (d, J=2.5 Hz, 1H), 8.04 (d, J=3.2 Hz, 1H), 7.88 (d, J=8.5 Hz, 1H), 7.74 (s, 1H), 7.51 (dd, J=8.2, 2.3 Hz, 1H), 2.25 (s, 3H), 1.47 (s, 9H); MS (EI/CI) m/z: 325.1 [M+H].

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe residue obtained
  3. customThe yellow precipitate formed
  4. filtrationwas collected by filtration
  5. customdried
  6. customThe mother liquor was purified by chromatography (silica, 5-25% of a 1:4 methanol:dichloromethane solution in dichloromethane)

Sources & evidence

ORD record
ord-515251ffd5d84162ae54d0a349a01501
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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