Lithium Hydroxide → 4-(5-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-chloro-N-cyclohexylpyridin-2-amine

HRID 2089028Notes

Reaction equation

HRID 2089028 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([C:24]4[CH:25]=[N:26][N:27](S(C5C=CC=CC=5)(=O)=O)[CH:28]=4)[CH:22]=3)[N:17](S(C3C=CC=CC=3)(=O)=O)[CH:16]=2)[CH:3]=1.[OH-].[Li+]>O1CCCC1.CO.O.C(OCC)(=O)C>[NH:26]1[CH:25]=[C:24]([C:21]2[CH:22]=[C:23]3[C:15]([C:4]4[CH:3]=[C:2]([Cl:1])[N:7]=[C:6]([NH:8][CH:9]5[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]5)[CH:5]=4)=[CH:16][NH:17][C:18]3=[N:19][CH:20]=2)[CH:28]=[N:27]1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 87192311HCID 87192311, compound

Product 1

HCID 871912104-(5-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-chloro-N-cyclohexylpyridin-2-amineYield 23.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of Example 171b (0.110 g, 0.16 mmol) in 18 mL tetrahydrofuran/methanol (2:1) was treated with 1N lithium hydroxide (0.048 g, 2.00 mmol) in 2 mL water at room temperature for 4 hours. The material was diluted with ethyl acetate, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by trituration with diethyl ether/ethyl acetate and filtration to afford 15 mg of the title compound. 1H NMR (400 MHz, DMSO-d6) ppm 1.17-1.44 (m, 5H) 1.56-1.66 (m, 1H) 1.69-1.80 (m, 2H) 1.92-2.01 (m, 2H) 3.66-3.78 (m, 1H) 6.39 (d, J=7.63 Hz, 1H) 6.83 (d, J=6.71 Hz, 2H) 7.95 (s, 1H) 7.95-8.16 (m, 2H) 8.33 (s, 1H) 8.52 (s, 1H) 11.79 (s, 1H) 12.73 (s, 1H). MS (ESI+) m/z 393.7 (M+H)+.

Workup

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. filtrationThe residue was purified by trituration with diethyl ether/ethyl acetate and filtration

Sources & evidence

ORD record
ord-972b19f7ccbb47e998dbe5246c6e18f4
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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