Sodium Bicarbonate → HCID 16064351, compound

HRID 1991123Notes

Reaction equation

HRID 1991123 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:50](=[O:56])[O:51][C:52]([CH3:55])([CH3:54])[CH3:53])[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.C([O-])(O)=O.[Na+]>>[NH:35]1[CH:39]=[C:38]([C:40]2[C:48]3[C:43](=[N:44][CH:45]=[C:46]([NH:49][C:50](=[O:56])[O:51][C:52]([CH3:54])([CH3:53])[CH3:55])[CH:47]=3)[NH:42][CH:41]=2)[CH:37]=[N:36]1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 160643543-(Furan-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-amineHCID 59128676HCID 59128676, compound

Product 1

HCID 16064351HCID 16064351, compoundYield 14.3%

Procedure

Inhibitor 52 was synthesized following the method described for preparation of 48 using 51 (326 mg, 0.60 mmol). The crude reaction mixture was neutralised with saturated aqueous NaHCO3 and extracted with AcOEt. Combined organic extracts were dried (MgSO4), concentrated and purified 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 52 (25.62 mg, 14%). 1H NMR (400 MHz; CDCl3+3 drops of CD3OD) δ 1.54 (s, 9H), 7.54 (s, 1H), 7.93 (s, 2H) 8.18 (d, J=2.1 Hz, 1H), 8.31 (d, J=2.1 Hz, 1H); MS (ES) m/z 341 (MH++MeCN).

Workup

  1. customInhibitor 52 was synthesized
  2. customThe crude reaction mixture
  3. extractionextracted with AcOEt
  4. dry with materialCombined organic extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by means of LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm)

Sources & evidence

ORD record
ord-f5d8506ae2d9454e80b316a29ec5ae9d
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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