1-Methylpiperazine → HCID 22019117, compound

HRID 1985771Notes

Reaction equation

HRID 1985771 reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][C:9]2[S:10][C:11]([CH2:14][NH:15][C:16]3[C:17]([F:29])=[CH:18][C:19]([F:28])=[C:20]([CH:27]=3)[C:21]([NH:23][CH:24]3[CH2:26][CH2:25]3)=[O:22])=[CH:12][N:13]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1>C(Cl)Cl>[CH:24]1([NH:23][C:21](=[O:22])[C:20]2[CH:27]=[C:16]([NH:15][CH2:14][C:11]3[S:10][C:9]([NH:8][C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([N:34]5[CH2:35][CH2:36][N:31]([CH3:30])[CH2:32][CH2:33]5)[N:7]=4)=[N:13][CH:12]=3)[C:17]([F:29])=[CH:18][C:19]=2[F:28])[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 220190675-{[2-(6-bromo-pyridin-2-ylamino)-thiazol-5-ylmethyl]-amino}-N-cyclopropyl-2,4-difluoro-benzamide

Product 1

HCID 22019117HCID 22019117, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-{[2-(6-bromo-pyridin-2-ylamino)-thiazol-5-ylmethyl]-amino}-N-cyclopropyl-2,4-difluoro-benzamide (96 mg, 0.20 mmol) in neat N-methyl piperazine (0.4 mL) was heated to 120° C. in a sealed tube for 5 h. The reaction mixture was cooled to RT, diluted with methylene chloride (5 mL), and washed with water (2×5 mL). The organic layer was dried over Na2SO4, concentrated, and the residue was purified by silica gel eluted with 2-10% MeOH/CH3Cl to give the title compound (53 mg, 55%) as a light yellow solid. (M+H)+=500.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. washwashed with water (2×5 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customthe residue was purified by silica gel
  6. washeluted with 2-10% MeOH/CH3Cl

Sources & evidence

ORD record
ord-fb7d2a77773840ff9612cb32ff67de37
Source dataset
uspto-grants-2009_06
Patent number
US07547711B2

Reaction notes

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