Diethyl Ether → HCID 73295272, compound

HRID 522949Notes

Reaction equation

HRID 522949 reaction equation
[OH:1][CH2:2][C:3]([NH:6][C:7]([C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)[N:16]=2)[N:11](COCC[Si](C)(C)C)[CH:10]=1)=[O:8])([CH3:5])[CH3:4].FC(F)(F)C(O)=O.CCOCC>ClCCl>[OH:1][CH2:2][C:3]([NH:6][C:7]([C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=3)[N:16]=2)[NH:11][CH:10]=1)=[O:8])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 90041616HCID 90041616, compound

Product 1

HCID 73295272HCID 73295272, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(1-hydroxy-2-methylpropan-2-yl)-2-(5-methylpyridin-2-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (66 mg, 140 μmol) in dichloromethane (1.5 mL) was added trifluoroacetic acid (320 mg, 216 μL, 2.8 mmol) and the mixture stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo then the residue was dissolved in dichloromethane (2 mL), methanol (0.5 mL) and ammonium hydroxide (0.3 mL). After stirring at room temperature for 30 min, the mixture was concentrated in vacuo and triturated with ether and water. The yellow precipitate was collected by filtration and washed with water then ether to give N-(1-hydroxy-2-methylpropan-2-yl)-2-(5-methylpyridin-2-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (31 mg, 91.1 μmol, 65%) as a yellow solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.38 (s, 1H), 9.86 (s, 1H), 8.39 (s, 1H), 8.12 (d, J=2.5 Hz, 1H), 8.04 (d, J=3.3 Hz, 1H), 7.95 (d, J=8.4 Hz, 1H), 7.74 (s, 1H), 7.54 (dd, J=8.6, 2.3 Hz, 1H), 5.06 (s, 1H), 3.58 (s, 2H), 2.25 (s, 3H), 1.39 (s, 6H); MS (EI/CI) m/z: 341.1 [M+H].

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane (2 mL)
  3. stirringAfter stirring at room temperature for 30 min
  4. concentrationthe mixture was concentrated in vacuo
  5. customtriturated with ether and water
  6. filtrationThe yellow precipitate was collected by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-4ebcf2d1b72043cb9a04e7584bb8adde
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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