2-Hydroxy-N,N-dimethyl-2-{5-[3-(2-methyl-2H-pyrazol-3-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-(2-methyl-2H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide

HRID 886630Notes

Reaction equation

HRID 886630 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[N:24]([CH3:28])[N:25]=[CH:26][CH: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[N:24]([CH3:28])[N:25]=[CH:26][CH:27]=4)=[CH:21][NH:20][C:17]3=[N:18][CH:19]=2)[CH:13]=1)[C:3]([N:5]([CH3:7])[CH3:6])=[O:4]

Participants

3

Reactant 1

HCID 598250742-Hydroxy-N,N-dimethyl-2-{5-[3-(2-methyl-2H-pyrazol-3-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide

Product 1

HCID 1360142832-hydroxy-N,N-dimethyl-2-{5-[3-(2-methyl-2H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamideYield 87.7%

Reagents, catalysts & solvents 1

HCID 22481192Dichloromethane trifluoroacetateSolvent

Procedure

2-Hydroxy-N,N-dimethyl-2-{5-[3-(2-methyl-2H-pyrazol-3-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide (71 mg, 0.1 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 material was stirred in dichloromethane/ethylenediamine (1 ml/1 ml) for 2 hours at room temperature. The solvents were removed in vacuo and the residue was dissolved in DMSO, filtered and purified by reverse phase HPLC and lyophilized to afford 2-hydroxy-N,N-dimethyl-2-{5-[3-(2-methyl-2H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide (33 mg, 61% yield). 1H NMR (500 MHz, DMSO-d6) δ 2.87 (s, 3H), 3.00 (s, 3H), 3.93 (s, 3H), 7.53 (m, 1H), 7.94 (s, 1H), 8.12 (m, 1H), 8.25 (m, 1H), 8.56 (m, 1H), 8.65 (m, 1H), 8.92 (m, 1H), 12.38 (s, 1H). MS: m/z 377.2 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-9adf80b716f24e9782c19c2652d15ee3
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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