Trifluoroacetic acid → HCID 73296111, compound

HRID 522997Notes

Reaction equation

HRID 522997 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:20]=[N:21][CH:22]=[CH:23][CH:24]=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>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:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[N:16]=2)[NH:11][CH:10]=1)=[O:8])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90040937HCID 90040937, compound

Product 1

HCID 73296111HCID 73296111, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(1-Hydroxy-2-methylpropan-2-yl)-2-(pyridin-3-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (32 mg, 70.1 μmol) was dissolved in dichloromethane (1.2 mL) and treated with trifluoroacetic acid (160 mg, 108 μL, 1.4 mmol). The mixture was stirred at room temperature for 16 h. The mixture was concentrated then re-dissolved in dichloromethane (1 mL), methanol (0.5 mL) and ammonium hydroxide (0.2 mL) and the mixture stirred at room temperature for 1 h. The mixture was concentrated in vacuo then triturated with water and filtered. The solid obtained was washed with ether then dried to give N-(1-hydroxy-2-methylpropan-2-yl)-2-(pyridin-3-ylamino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (21 mg, 64.3 μmol, 92%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d) 6 ppm: 12.39 (s, 1H), 9.66 (s, 1H), 8.85 (d, J=2.5, 1 H), 8.21 (m, 1H), 8.16 (dd, J=4.7, 1.6, 1 H), 8.04 (s, 1H), 8.03 (s, 1H), 7.67 (s, 1H), 7.33 (m, 1H), 5.05 (t, J=5.6, 1 H), 3.58 (d, J=5.9, 2 H), 1.36 (s, 6H); MS (EI/CI) m/z: 327.1 [M+H].

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthen re-dissolved in dichloromethane (1 mL)
  3. stirringmethanol (0.5 mL) and ammonium hydroxide (0.2 mL) and the mixture stirred at room temperature for 1 h
  4. concentrationThe mixture was concentrated in vacuo
  5. customthen triturated with water
  6. filtrationfiltered
  7. customThe solid obtained
  8. washwas washed with ether
  9. customthen dried

Sources & evidence

ORD record
ord-8e4848251d2141fdb0e2f6864dc160da
Source dataset
uspto-grants-2016_05
Patent number
US09334278B2

Reaction notes

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