Acetic Acid → 2-amino-3-fluoro-5-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide

HRID 2234634Notes

Reaction equation

HRID 2234634 reaction equation
[NH2:1][C:2]1[C:12]([F:13])=[CH:11][C:10]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH3:30])=[CH:21][N:20](S(C4C=CC(C)=CC=4)(=O)=O)[C:17]3=[N:18][CH:19]=2)=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].[OH-].[K+].C(O)(=O)C>CO>[NH2:1][C:2]1[C:12]([F:13])=[CH:11][C:10]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH3:30])=[CH:21][NH:20][C:17]3=[N:18][CH:19]=2)=[CH:9][C:3]=1[C:4]([N:6]([CH3:7])[CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 577314782-amino-3-fluoro-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide

Product 1

HCID 250610602-amino-3-fluoro-5-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamideYield 62.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

222 mg (0.397 mmol) of 2-amino-3-fluoro-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide was dissolved in 5 mL methanol and 200 μL of a 50% w/v potassium hydroxide aqueous solution was added. The mixture was stirred at room temperature for 5.5 hours and then neutralized with acetic acid. The material was filtered through a 0.45 μm syringe filter and purified by mass-triggered reverse phase HPLC in a gradient of acetonitrile and water (containing 0.1% formic acid). The clean fractions were lyophilized to afford 100 mg (0.247 mmol, 62% yield) of 2-amino-3-fluoro-5-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide as an off-white powder. 1H NMR (500 MHz, DMSO-d6) δ 11.79 (d, 1H), 8.41 (d, 1H), 8.02 (d, 1H), 7.65 (d, 1H), 7.56 (dd, 1H), 7.45 (dd, 1H), 7.22 (t, 1H), 7.15 (d, 1H), 7.07 (d, 1H), 6.99 (t, 1H), 5.17 (s, 2H), 3.75 (s, 3H), 2.90 (s, br., 6H); MS: m/z 405.1 (M+H+).

Workup

  1. filtrationThe material was filtered through a 0.45 μm syringe
  2. filtrationfilter
  3. custompurified by mass-triggered reverse phase HPLC in a gradient of acetonitrile and water (containing 0.1% formic acid)

Sources & evidence

ORD record
ord-bae7a23c2585436aa83d25f004f6ccd5
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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