Hydrochloric Acid → 3-(Furan-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine

HRID 1991121Notes

Reaction equation

HRID 1991121 reaction equation
Cl.[O:2]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([NH:16]C(=O)OC(C)(C)C)[CH:14]=3)[NH:9][CH:8]=2)=[CH:3]1>CO>[O:2]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([NH2:16])[CH:14]=3)[NH:9][CH:8]=2)=[CH:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 16064352HCID 16064352, compound

Product 1

HCID 160643543-(Furan-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-amineYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.0 M aqueous HCl (0.83 mL, 3.32 mmol) was added to a suspension of 47 (90 mg, 0.30 mmol) in MeOH (0.17 mL) and the mixture was stirred at r.t. overnight. Concentrated aqueous HCl (0.2 mL, 2.2 mmol) was added and stirring continued for 5 h. The mixture was concentrated to dryness in vacuum and separated by means of LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm) using water—MeCN (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to afford 48 (41.64 mg, 70%). 1H NMR (400 MHz; CDCl3+3 drops of CD3OD) δ 6.61 (dd, J=1.8, 0.8 Hz, 1H), 7.32 (s, 1H), 7.43 (d, J=2.5 Hz, 1H), 7.45 (dd, J=3.3, 1.7 Hz, 1H), 7.68 (dd, J=2.3, 1.0 Hz, 1H), 7.80 (d, J=2.5 Hz, 1H); MS (ES) m/z 241 (MH++MeCN).

Workup

  1. stirringstirring
  2. waitcontinued for 5 h
  3. concentrationThe mixture was concentrated to dryness in vacuum
  4. customseparated by means of LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm)

Sources & evidence

ORD record
ord-8bdb3c80b3cc49d9be0f1d950a43e798
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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