Hydrochloric Acid → 1-{4-[2-Cyclopentyl-1-(5-methoxy-thiazolo[5,4-b]pyridin-2-ylcarbamoyl)-ethyl]-benzenesulfonyl}-piperidine-4-carboxylic acid

HRID 1712995Notes

Reaction equation

HRID 1712995 reaction equation
[OH-].[Na+].C([O:5][C:6]([CH:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]([C:30](=[O:43])[NH:31][C:32]3[S:33][C:34]4[C:39]([N:40]=3)=[CH:38][CH:37]=[C:36]([O:41][CH3:42])[N:35]=4)[CH2:24][CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])C.Cl>O.CO>[CH:25]1([CH2:24][CH:23]([C:20]2[CH:19]=[CH:18][C:17]([S:14]([N:11]3[CH2:12][CH2:13][CH:8]([C:6]([OH:7])=[O:5])[CH2:9][CH2:10]3)(=[O:16])=[O:15])=[CH:22][CH:21]=2)[C:30](=[O:43])[NH:31][C:32]2[S:33][C:34]3[C:39]([N:40]=2)=[CH:38][CH:37]=[C:36]([O:41][CH3:42])[N:35]=3)[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 866257401-{4-[2-Cyclopentyl-1-(5-methoxy-thiazolo[5,4-b]pyridin-2-ylcarbamoyl)-ethyl]-benzenesulfonyl}-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 594634831-{4-[2-Cyclopentyl-1-(5-methoxy-thiazolo[5,4-b]pyridin-2-ylcarbamoyl)-ethyl]-benzenesulfonyl}-piperidine-4-carboxylic acidYield 73.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium hydroxide (12 mg, 0.2996 mmol) was dissolved in a minimum amount of water and added to a solution of title compound F, 1-{4-[2-Cyclopentyl-1-(5-methoxy-thiazolo[5,4-b]pyridin-2-ylcarbamoyl)-ethyl]-benzenesulfonyl}-piperidine-4-carboxylic acid ethyl ester (90 mg, 0.1498 mmol) in methanol. The reaction was stirred at room temperature overnight, poured into 1N hydrochloric acid, and extracted with ethyl acetate. Extracts were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford the title compound as a yellow foam (63 mg, 73%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.05-1.16 (m, 2 H) 1.36-1.47 (m, 2 H) 1.49-1.61 (m, 5 H) 1.66-1.72 (m, 3 H) 1.75 (s, 1 H) 1.78-1.80 (m, 1 H) 1.92-2.02 (m, 1 H) 2.08-2.18 (m, 1 H) 2.40 (t, J=9.85 Hz, 2 H) 3.35 (d, J=11.37 Hz, 2 H) 3.82-3.92 (m, 4 H) 6.74 (d, J=8.59 Hz, 1 H) 7.59-7.67 (m, 4 H) 7.79 (d, J=8.84 Hz, 1 H) LC/MS 573.1 (M+1) 571.4 (M−1) EC50 in primary enzyme assay 7.1 μM

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a984d662b1124a57a9bba4809440b3ab
Source dataset
uspto-grants-2010_09
Patent number
US07795257B2

Reaction notes

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