3-(Furan-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine → 3-(1H-Pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine

HRID 1991124Notes

Reaction equation

HRID 1991124 reaction equation
O1C=CC(C2C3C(=NC=C(N)C=3)NC=2)=C1.C([N:35]1[CH:39]=[C:38]([C:40]2[C:48]3[C:43](=[N:44][CH:45]=[C:46]([NH:49]C(=O)OC(C)(C)C)[CH:47]=3)[NH:42][CH:41]=2)[CH:37]=[N:36]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>>[NH:35]1[CH:39]=[C:38]([C:40]2[C:48]3[C:43](=[N:44][CH:45]=[C:46]([NH2:49])[CH:47]=3)[NH:42][CH:41]=2)[CH:37]=[N:36]1

Participants

3

Reactant 2

HCID 160643543-(Furan-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-amineHCID 59128676HCID 59128676, compound

Product 1

HCID 160643553-(1H-Pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amineYield 11%

Procedure

Inhibitor 53 was synthesized following the method described for preparation of 48 using 51 (150 mg, 0.28 mmol). The reaction 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 53 (6.07 mg, 11%). 1H NMR (400 MHz; CDCl3+3 drops of CD3OD) δ 7.26 (s, 1H), 7.66 (s, 2H), 8.54 (d, J=1.9 Hz, 1H), 8.68 (d, J=1.9 Hz, 1H); MS (ES) m/z 241 (MH++MeCN).

Workup

  1. customInhibitor 53 was synthesized
  2. concentrationThe reaction mixture was concentrated to dryness in vacuum
  3. customseparated by means of LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm)

Sources & evidence

ORD record
ord-e10c9a6230df4a82814993eb4c5f0d34
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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