Sodium Hydroxide → 5-(Butylsulfanyl)-3-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 1991100Notes

Reaction equation

HRID 1991100 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([S:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:18]=[C:13]3[C:12]([C:24]3[CH:25]=[N:26][NH:27][CH:28]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>C(O)C>[CH2:20]([S:19][C:17]1[CH:18]=[C:13]2[C:12]([C:24]3[CH:25]=[N:26][NH:27][CH:28]=3)=[CH:11][NH:10][C:14]2=[N:15][CH:16]=1)[CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59128682HCID 59128682, compound

Product 1

HCID 160647945-(Butylsulfanyl)-3-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineYield 35.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Inhibitor 17 was synthesized following the method described for preparation of 8 using 16 (0.50 g, 1.21 mmol), ethanol (23 mL), 10% aq. NaOH (11.2 mL). Reaction time: 1 h at 90° C. Purification by SGC using CH2Cl2:MeOH (gradient elution up to 97:3, v/v) gave 17 as an orange foam (116 mg, 35%); 1H NMR (400 MHz, CDCl3) δ 0.87 (t, J=7.3 Hz, 3H), 1.39 (sextet, J=7.4 Hz, 2H), 1.55 (quintet, J=7.4 Hz, 2H), 2.84 (t, J=7.4 Hz, 2H), 7.42 (s, 1H), 7.83 (s, 2H), 8.19 (d, J=2.0 Hz, 1H), 8.36 (dd, J=2.0, 0.3 Hz, 1H).

Workup

  1. customInhibitor 17 was synthesized
  2. customReaction time
  3. custom1 h
  4. customat 90° C
  5. customPurification by SGC
  6. washMeOH (gradient elution up to 97:3

Sources & evidence

ORD record
ord-1fd5dae0ae844b31969be2ceda9f5cbe
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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