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

HRID 1011742
Notes
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Reaction equation

HRID 1011742 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-c14dafdc5e554714960b3bde39193c4c
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07977328B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes