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Sodium Hydroxide → 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxy piperidin-1-yl]-4-[5-(piperidin-1-yl)pyrazin-2-yl]-1,3-thiazole-5-carboxylic acid

HRID 655740
Notes
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Reaction equation

HRID 655740 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:35]([O:37]CC)=[O:36])=[C:21]([C:23]3[CH:28]=[N:27][C:26]([N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)=[CH:25][N:24]=3)[N:22]=2)[CH2:14][C@@H:13]1[O:40][CH2:41][CH3:42])=[O:10].[OH-].[Na+]>CO>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:35]([OH:37])=[O:36])=[C:21]([C:23]3[CH:28]=[N:27][C:26]([N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)=[CH:25][N:24]=3)[N:22]=2)[CH2:14][C@@H:13]1[O:40][CH2:41][CH3:42])=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59402461ethyl 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl]-4-[5-(piperidin-1-yl)pyrazin-2-yl]-1,3-thiazole-5-carboxylate

Product 1

HCID 594025252-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxy piperidin-1-yl]-4-[5-(piperidin-1-yl)pyrazin-2-yl]-1,3-thiazole-5-carboxylic acidYield 31.8%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

To the solution of ethyl 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl]-4-[5-(piperidin-1-yl)pyrazin-2-yl]-1,3-thiazole-5-carboxylate (Example 67, 120 mg, 0.188 mmol) in methanol (20 mL) was added 2N sodium hydroxide (3 mL) in a dropwise fashion at 0° C. The reaction mixture was stirred overnight and then concentrated under reduced pressure to dryness. The resulting residue was diluted with water (20 mL) and extracted with ethyl acetate to remove any organic impurities. The aqueous layer was passed through celite bed and acidified with 2N hydrochloric acid. The precipitated product was collected by filtration and dried to afford 35 mg (31.8%) of 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxy piperidin-1-yl]-4-[5-(piperidin-1-yl)pyrazin-2-yl]-1,3-thiazole-5-carboxylic acid as a yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure to dryness
  2. additionThe resulting residue was diluted with water (20 mL)
  3. extractionextracted with ethyl acetate
  4. customto remove any organic impurities
  5. filtrationThe precipitated product was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-fae2bf4e7a584e38937584258980d524
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08071605B2

Reaction notes

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