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Potassium Hydroxide → HCID 57731584, compound

HRID 2234718
Notes
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Reaction equation

HRID 2234718 reaction equation
[CH3:1][N:2]([CH3:50])[C:3]([C:5]1[CH:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH3:27])=[CH:18][N:17](S(C4C=CC(C)=CC=4)(=O)=O)[C:14]3=[N:15][CH:16]=2)[CH:8]=[CH:7][C:6]=1[NH:38][C:39]([CH:41]1[CH2:46][CH2:45][CH2:44][N:43]([CH:47]([CH3:49])[CH3:48])[CH2:42]1)=[O:40])=[O:4].[OH-].[K+]>CO.CN(C)C=O>[CH3:50][N:2]([CH3:1])[C:3]([C:5]1[CH:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH3:27])=[CH:18][NH:17][C:14]3=[N:15][CH:16]=2)[CH:8]=[CH:7][C:6]=1[NH:38][C:39]([CH:41]1[CH2:46][CH2:45][CH2:44][N:43]([CH:47]([CH3:48])[CH3:49])[CH2:42]1)=[O:40])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 57731525HCID 57731525, compound

Product 1

HCID 57731584HCID 57731584, compoundYield 31.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

1-iso-Propyl-piperidine-3-carboxylic acid {2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-amide (185.1 mg, 0.27 mmol) was dissolved in methanol (0.5 mL) and dimethylformamide (0.5 mL), cooled to 0° C. and 50% w/v aqueous potassium hydroxide (0.2 mL) was added. After 1 hour, the reaction was quenched by addition of concentrated hydrochloric acid (0.2 mL). The mixture was carefully poured into saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and dried to a residue which was purified by preparative HPLC to afford 1-isopropyl-piperidine-3-carboxylic acid {2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-amide (46.0 mg, 31.9%). 1H-NMR (500 MHz, dimethylsulfoxide-d6) δ 0.98 (d, J=6.5 Hz, 6H), 1.59 (m, 2H), 1.76 (m, 2H), 2.16 m, 3H, 2.32 (m, 2H), 2.70 (m, 1H, 2.87 (s, 3H), 2.97 (s, 3H, 3.82 (s, 3H), 7.04 (t, J=7.5 Hz, 1H), 7.09 (d, J=8.0 Hz, 1H), 7.28 (dt, J=1.5, J=7.5 Hz 1H), 7.61 (dd, J=1.5 Hz, J=7.5 Hz, 1H), 7.59-7.61 (m, 2H), 7.65 (d, J=8.0 Hz, 1H), 7.72-7.74 (m, 2H), 8.54 (d, J=2.5 Hz, 1H), 9.51 (s, 1H), 11.92 (s, 1H). MS: m/z 541 (M+H+).

Workup

  1. additionwas added
  2. customthe reaction was quenched by addition of concentrated hydrochloric acid (0.2 mL)
  3. additionThe mixture was carefully poured into saturated sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. customdried to a residue which
  8. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-f31057caee4b4e7bab8a086a54c23935
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07709645B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes