Water → HCID 178523500, compound

HRID 1093811Notes

Reaction equation

HRID 1093811 reaction equation
S(=O)(=O)(O)N.[CH:6]([C:8]1[CH:37]=[CH:36][CH:35]=[CH:34][C:9]=1[O:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:33])[CH2:18][NH:19][C:20]([C:22]2[CH:26]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[NH:24][N:23]=2)=[O:21])[CH2:13][CH2:12]1)=[O:7].Cl([O-])=[O:39].[Na+].O>CC(C)=O>[C:27]1([C:25]2[NH:24][N:23]=[C:22]([C:20]([NH:19][CH2:18][C:17]([N:14]3[CH2:15][CH2:16][CH:11]([O:10][C:9]4[CH:34]=[CH:35][CH:36]=[CH:37][C:8]=4[C:6]([OH:39])=[O:7])[CH2:12][CH2:13]3)=[O:33])=[O:21])[CH:26]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5987Sulfamic AcidHCID 23668197Sodium ChloriteHCID 178519541HCID 178519541, compound

Product 1

HCID 178523500HCID 178523500, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sulphamic acid (34 mg, 0.3 mmol) was added to stirred a mixture of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-formyl-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide (50 mg, 0.1 mmol) in acetone (1 mL). After 2 minutes, sodium chlorite (36 mg, 0.4 mmol) was added and the resulting mixture was stirred at ambient temperature for 1 hour. Water was added and the solid obtained was isolated by filtration to afford 24 mg (53% yield) of 2-(1-{2-[(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetyl}-piperidin-4-yloxy)-benzoic acid. LC/MS [M+H]+: 449.17, 90.6%, 1H NMR (300 MHz, DMSO-d6): δ13.8 (b, 1H), 12.8 (b, 1H), 8.1 (m, 1H), 7.8 (m, 2H), 7.6 (m, 1H), 7.5 (m, 3H), 7.4 (m, 1H), 7.2 (m, 1H), 7.1 (m, 1H), 7.0 (m, 1H), 4.8 (m, 1H), 4.2 (m, 2H), 3.7 (m, 3H), 3.5 (m, 1H), 2.0 (m, 1H), 1.7 (m, 3H).

Workup

  1. stirringthe resulting mixture was stirred at ambient temperature for 1 hour
  2. customthe solid obtained
  3. customwas isolated by filtration

Sources & evidence

ORD record
ord-26515f67274a4f8287d91938ed8a7142
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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