Trifluoroacetic acid → HCID 73295445, compound

HRID 522965Notes

Reaction equation

HRID 522965 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:19]=[N:20][CH:21]=[CH:22][CH:23]=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>ClCCl.CO.[OH-].[NH4+]>[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:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735553HCID 131735553, compound

Product 1

HCID 73295445HCID 73295445, compoundYield 77.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 14923Ammonium HydroxideSolvent

Procedure

To a solution of N-tert-butyl-2-(pyridin-3-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (44 mg, 99.9 mol) in dichloromethane (1.6 mL) was added trifluoroacetic acid (228 mg, 154 μL, 2.00 mmol) and the reaction mixture stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo and the residue obtained diluted with dichloromethane (1.6 mL), methanol (0.8 mL) and ammonium hydroxide (0.2 mL) and stirred at room temperature for 1 h. The mixture was concentrated and triturated with water. The solid was collected by filtration and washed with water and ether to give N-tert-butyl-2-(pyridin-3-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (24 mg, 77.3 mol, 77%) as a brown solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.26 (s, 1H), 9.54 (s, 1H), 8.77 (d, J=2.5, 1 H), 8.04 (d, J=4.6, 1 H), 7.98 (d, J=8.5, 1 H), 7.92 (d, J=3.3, 1 H), 7.91 (s, 1H), 7.57 (s, 1H), 7.19 (m, 1H), 1.31 (s, 9H); MS (EI/CI) m/z: 311.1 [M+H].

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue obtained
  3. stirringstirred at room temperature for 1 h
  4. concentrationThe mixture was concentrated
  5. customtriturated with water
  6. filtrationThe solid was collected by filtration
  7. washwashed with water and ether

Sources & evidence

ORD record
ord-0b7c41de0d3f480882505cf10beb6ca5
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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