1-Methylpiperazine → HCID 91182712, compound

HRID 2242362Notes

Reaction equation

HRID 2242362 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][NH:9][C:10]([C:12]1[N:13]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26](Br)[CH:25]=2)[C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([C:21]#[N:22])=[CH:16][CH:15]=2)=[O:11].BrC1C=C(C=CC=1)CBr.NCC(C)(C)CO.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:55][N:56]1[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]1>COCCOC>[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:8][NH:9][C:10]([C:12]1[N:13]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N:59]3[CH2:60][CH2:61][N:56]([CH3:55])[CH2:57][CH2:58]3)[CH:25]=2)[C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([C:21]#[N:22])=[CH:16][CH:15]=2)=[O:11]

Participants

7

Reactant 5

HCID 531671-MethylpiperazineHCID 62657Potassium Phosphate, TribasicHCID 699793-Bromobenzyl bromideHCID 1173261-Propanol, 3-amino-2,2-dimethyl-HCID 72530828HCID 72530828, compound

Product 1

HCID 91182712HCID 91182712, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-cyano-1-[3-bromobenzyl]-1H-indole-2-carboxylic acid (2-hydroxy-cyclohexylmethyl)amide (prepared using 3-bromobenzyl bromide and 3-amino-2,2-dimethyl-1-propanol in a manner similar to that described in Example 35) (0.250 g, 0.54 mmol), tris(dibenzylidineacetone)dipalladium (125 mg, 0.014 mmol), 2-(dicyclohexylphosphine) biphenyl (9.6 mg, 0.027 mmol), potassium phosphate (1.44 g, 0.82 mmol) and N-methylpiperazine (64 mg, 0.64 mmol) in 1,2-dimethoxyethane (3 ml) were heated in a sealed Reactavial at 100° C. under nitrogen for 30 h. After cooling to ambient temperature, the mixture was filtered through dicalite and the resulting filtrate evaporated to dryness. Purification was fulfilled by chromatography on silica using DCM:methanol (19:1) as eluent, affording the title compound (0.021 g, 8%).

Workup

  1. customprepared
  2. temperatureAfter cooling to ambient temperature
  3. filtrationthe mixture was filtered through dicalite
  4. customthe resulting filtrate evaporated to dryness
  5. customPurification

Sources & evidence

ORD record
ord-41ef98f27ab44b2c92ca141c0d6c64fc
Source dataset
uspto-grants-2010_03
Patent number
US07671080B2

Reaction notes

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