Methanol → HCID 73295273, compound

HRID 522951Notes

Reaction equation

HRID 522951 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:22]=[CH:21][N:20]([CH3:23])[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:22]=[CH:21][N:20]([CH3:23])[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 131735547HCID 131735547, compound

Product 1

HCID 73295273HCID 73295273, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-tert-butyl-2-(1-methyl-1H-pyrazol-3-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (140 mg, 316 μmol) in dichloromethane (3.5 mL) was added trifluoroacetic acid (720 mg, 486 μL, 6.31 mmol) and the mixture stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo and the residue obtained dissolved in dichloromethane (3 mL), methanol (1.5 mL), and ammonium hydroxide (0.65 mL) and the mixture stirred at room temperature for 1 h. The mixture was concentrated in vacuo then triturated with ether and water. The solid was collected by filtration then dried in vacuo to give N-tert-butyl-2-(1-methyl-1H-pyrazol-3-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (44 mg, 140 μmol, 45%) as a brown solid. 1H NMR (400 MHz, methanol-d) δ ppm: 8.07 (s, 1H), 7.93 (s, 1H), 7.81 (s, 1H), 7.35 (d, J=2.2 Hz, 1H), 6.32 (d, J=2.2 Hz, 1H), 3.67 (s, 3H), 1.35 (s, 9H); MS (EI/CI) m/z: 314.1 [M+H].

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue obtained
  3. concentrationThe mixture was concentrated in vacuo
  4. customthen triturated with ether and water
  5. filtrationThe solid was collected by filtration
  6. customthen dried in vacuo

Sources & evidence

ORD record
ord-1a62e302673d40569df4749109f98b6b
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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