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Ammonium formate → 3-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide

HRID 1175913
Notes
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Reaction equation

HRID 1175913 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:29])[C:9]2[CH:14]=[C:13]([O:15][C@H:16]3[CH2:20][CH2:19][O:18][CH2:17]3)[CH:12]=[C:11]([O:21]CC3C=CC=CC=3)[CH:10]=2)=[N:3]1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[OH:21][C:11]1[CH:10]=[C:9]([CH:14]=[C:13]([O:15][C@H:16]2[CH2:20][CH2:19][O:18][CH2:17]2)[CH:12]=1)[C:8]([NH:7][C:4]1[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=1)=[O:29]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 53629650N-(1-Methyl-1H-pyrazol-3-yl)-3-[(phenylmethyl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide

Product 1

HCID 591271713-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)-5-[(3S)-tetrahydrofuran-3-yloxy]benzamideYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702
Ethanol
Solvent

Conditions

Temperature
140 °C

Procedure

N-(1-Methyl-1H-pyrazol-3-yl)-3-[(phenylmethyl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide (453 mg, 1.15 mmol) was dissolved in ethanol (5 mL) and ammonium formate (182 mg, 2.88 mmol) was added in one portion. The reaction was blanketed with argon and 10% palladium on activated carbon (30 mg) was added. This mixture was heated to 140° C. for 10 minutes in a Smith Creator microwave. The catalyst was filtered off and the volatiles removed in vacuo to give the title product as a white solid (339 mg).

Workup

  1. additionwas added
  2. filtrationThe catalyst was filtered off
  3. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-6b9e69b0bf294051a543cf645e8a0d71
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07842694B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes