2-hydroxy-N,N-dimethyl-2-{5-[3-oxazol-2-yl-1(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide → 2-hydroxy-N,N-dimethyl-2-{5-[3-oxazol-2-yl-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide

HRID 886636Notes

Reaction equation

HRID 886636 reaction equation
[OH:1][CH:2]([C:8]1[CH:9]=[N:10][CH:11]=[C:12]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[O:24][CH:25]=[CH:26][N:27]=4)=[CH:21][N:20](COCC[Si](C)(C)C)[C:17]3=[N:18][CH:19]=2)[CH:13]=1)[C:3]([N:5]([CH3:7])[CH3:6])=[O:4]>ClCCl.FC(F)(F)C([O-])=O>[OH:1][CH:2]([C:8]1[CH:9]=[N:10][CH:11]=[C:12]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[O:24][CH:25]=[CH:26][N:27]=4)=[CH:21][NH:20][C:17]3=[N:18][CH:19]=2)[CH:13]=1)[C:3]([N:5]([CH3:6])[CH3:7])=[O:4]

Participants

3

Reactant 1

HCID 598250292-hydroxy-N,N-dimethyl-2-{5-[3-oxazol-2-yl-1(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide

Product 1

HCID 598248372-hydroxy-N,N-dimethyl-2-{5-[3-oxazol-2-yl-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamideYield 31%

Reagents, catalysts & solvents 1

HCID 22481192Dichloromethane trifluoroacetateSolvent

Procedure

2-Hydroxy-N,N-dimethyl-2-{5-[3-oxazol-2-yl-1(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide (10 mg, 0.02 mmol) was stirred in dichloromethane/trifluoroacetate acid (1 ml/1 ml) at room temperature for 2 hours. The solvents were removed under vacuum and the crude was stirred in dichloromethane/ethylenediamine (1 ml/1 ml) for 2 hours at room temperature. Again the solvents was removed under vacuum and the crude was dissolved in DMSO, filtered and purified by reverse phase HPLC, lyophilized afforded 2-hydroxy-N,N-dimethyl-2-{5-[3-oxazol-2-yl-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide (2 mg, 31% yield). 1H NMR (500 MHz, DMSO-d6) δ 2.81 (s, 3H), 2.96 (s, 3H), 5.58 (s, 1H), 6.22 (s, 1H), 7.28 (s, 1H), 8.04 (t, 1H), 8.76 (s, 1H), 8.22 (s, 1H), 8.52 (d, 1H), 8.62 (s, 2H0, 8.83 (d, 1H). MS: m/z 364.0 (M+H+).

Workup

  1. customThe solvents were removed under vacuum
  2. customAgain the solvents was removed under vacuum
  3. dissolutionthe crude was dissolved in DMSO
  4. filtrationfiltered
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-18971711016f4322bceddc1ebf743754
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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