HCID 21975635, compound → HCID 178426961, compound

HRID 2352897Notes

Reaction equation

HRID 2352897 reaction equation
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[N:24]([CH3:29])[N:25]=[C:26]([CH3:28])[CH:27]=4)=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:30].[F:31][CH:32]1[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][CH2:39][O:40][C:41]2[CH:46]=[CH:45][C:44]([NH2:47])=[CH:43][CH:42]=2)[CH2:33]1>C1COCC1>[F:31][CH:32]1[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][CH2:39][O:40][C:41]2[CH:42]=[CH:43][C:44]([NH:47][CH:2]=[C:3]3[C:11]4[C:6](=[CH:7][C:8]([C:12]([C:14]5[CH:15]=[C:16]([NH:20][C:21]([C:23]6[N:24]([CH3:29])[N:25]=[C:26]([CH3:28])[CH:27]=6)=[O:22])[CH:17]=[CH:18][CH:19]=5)=[O:13])=[CH:9][CH:10]=4)[NH:5][C:4]3=[O:30])=[CH:45][CH:46]=2)[CH2:33]1

Participants

4

Reactant 2

HCID 21975635HCID 21975635, compoundHCID 178426964HCID 178426964, compound

Product 1

HCID 178426961HCID 178426961, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 60, 100 mg, 0.249 mmol) and THF (2 mL). To the resulting solution was added 4-[3-(3-Fluoro-pyrrolidin-1-yl)-propoxy]-phenylamine (prepared below, 59.3 mg, 0.249 mmol), and the mixture was stirred for 24 h at 65° C. The reaction mixture was cooled to room temperature. Hexanes were added to the reaction mixture causing a black precipitate to form. The precipitate was vacuum filtered and the filtrate was then concentrated in vacuo and redissolved into ˜3 mL of EtOAc. Hexanes were added causing a yellow precipitate to form. The precipitate was then filtered and washed with 1 mL of i-prOH yielding 39% (0.060 g, 0.097 mmol) of the title compound.

Workup

  1. customA small screw cap test tube
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customto form
  4. filtrationfiltered
  5. concentrationthe filtrate was then concentrated in vacuo
  6. dissolutionredissolved into ˜3 mL of EtOAc
  7. additionHexanes were added
  8. customto form
  9. filtrationThe precipitate was then filtered

Sources & evidence

ORD record
ord-8b61434f3be7454283f7cacdc2800888
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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