Tetrahydrofuran → HCID 178426967, compound

HRID 2352857Notes

Reaction equation

HRID 2352857 reaction equation
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]4[N:24]([C:29]([CH3:32])([CH3:31])[CH3:30])[N:25]=[C:26]([CH3:28])[CH:27]=4)=[O:22])=[CH:16][CH:15]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:33].[NH2:34][C:35]1[CH:36]=[CH:37][C:38](OC)=[C:39]([OH:41])[CH:40]=1.[CH2:44]1COCC1>>[OH:41][C:39]1[CH:40]=[C:35]([NH:34][CH:2]=[C:3]2[C:11]3[C:6](=[CH:7][C:8]([C:12]([C:14]4[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]5[N:24]([C:29]([CH3:32])([CH3:31])[CH3:30])[N:25]=[C:26]([CH3:28])[CH:27]=5)=[O:22])=[CH:16][CH:15]=4)=[O:13])=[CH:9][CH:10]=3)[NH:5][C:4]2=[O:33])[CH:36]=[CH:37][C:38]=1[CH3:44]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 743145-Amino-2-methoxyphenolHCID 178426975HCID 178426975, compound

Product 1

HCID 178426967HCID 178426967, compoundYield 32%

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with 2-tert-Butyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 65, 100 mg, 0.225 mmol) and THF (2 mL). To the resulting solution was added 5-amino-2-methoxyphenol (34 mg, 0.25 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature. Hexanes were added to the reaction mixture. The solid precipitate that formed was washed with ˜1 mL of i-prOH yielding 32% (38 mg, 0.071 mmol) of the title compound.

Workup

  1. customA small screw cap test tube
  2. temperatureSubsequently, the reaction mixture was cooled to room temperature
  3. customThe solid precipitate that formed

Sources & evidence

ORD record
ord-4d4f75041e1c43a0afe258594a938538
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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