Diisopropylethylamine → HCID 69510757, compound

HRID 969668Notes

Reaction equation

HRID 969668 reaction equation
[CH3:1][C:2]1([CH3:23])[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:22])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N+:19]([O-:21])=[O:20])=[CH:8][CH:9]=2)[NH:4][CH2:3]1.[CH3:24][N:25]1[CH2:30][CH2:29][N:28]([C:31](Cl)=[O:32])[CH2:27][CH2:26]1.CCN(C(C)C)C(C)C>C1COCC1>[CH3:1][C:2]1([CH3:23])[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:22])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N+:19]([O-:21])=[O:20])=[CH:8][CH:9]=2)[N:4]([C:31]([N:28]2[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]2)=[O:32])[CH2:3]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 30169354-Methyl-1-piperazinecarbonyl chlorideHCID 69511218HCID 69511218, compound

Product 1

HCID 69510757HCID 69510757, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-2-nitro-benzamide (Example 7, Step A)(300 mg, 0.96 mmol) was treated with 4-methyl-piperazine-1-carbonyl chloride (200 mg, 1 mmol) in the presence of DIEA (40 mL) in THF overnight at 65° C. The mixture was partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was washed with H2O and brine, then dried over Na2SO4. The organic solution was concentrated in vacuo to yield the desired compound.

Workup

  1. customThe mixture was partitioned between EtOAc and saturated aqueous NaHCO3
  2. washThe organic layer was washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe organic solution was concentrated in vacuo

Sources & evidence

ORD record
ord-501add2a2da044bf8b9831f07c8e68a2
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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