Methanol → HCID 73295274, compound

HRID 522953Notes

Reaction equation

HRID 522953 reaction equation
[CH:1]([NH:4][C:5]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=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.CO.[OH-].[NH4+]>ClCCl>[CH:1]([NH:4][C:5]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=3)[N:14]=2)[NH:9][CH:8]=1)=[O:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 90041067HCID 90041067, compound

Product 1

HCID 73295274HCID 73295274, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-isopropyl-2-(5-methylpyridin-2-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (90 mg, 204 μmol) in dichloromethane (2.5 mL) was added trifluoroacetic acid (466 mg, 315 μL, 4.09 mmol) and stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo then the residue obtained was dissolved in dichloromethane (3 mL), methanol (1.5 mL) and ammonium hydroxide (0.45 mL). After 3 h at room temperature, the mixture was concentrated in vacuo then triturated with water and ether. The solid was collected by filtration to give N-isopropyl-2-(5-methylpyridin-2-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (23 mg, 74.1 μmol, 36%) as an off white solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.40 (s, 1H), 9.92 (s, 1H), 8.43 (s, 1H), 8.14 (s, 1H), 8.09 (d, J=3.2, 1 H), 7.86 (s, 1H), 7.85 (d, J=15.1 Hz, 1H), 7.55 (dd, J=8.5, 2.3 Hz, 1H), 4.16 (m, 1H), 2.26 (s, 3H), 1.25 (d, J=6.5, 6 H); MS (EI/CI) m/z: 311.1 [M+H].

Workup

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

Sources & evidence

ORD record
ord-4d8f1d0e1a59488a925a4d098f06239a
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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