Isopropylamine → HCID 23155692, compound

HRID 1714790Notes

Reaction equation

HRID 1714790 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]2[O:26][C:25](=[O:27])[C:24]3[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=3[N:22]=2)[CH2:13][CH2:12]1.[CH:32]([NH2:35])([CH3:34])[CH3:33]>O1CCCC1>[CH:32]([NH:35][C:25](=[O:27])[C:24]1[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=1[NH:22][C:21](=[O:26])[CH2:20][CH2:19][CH2:18][CH2:17][N:14]1[CH2:13][CH2:12][N:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH2:16][CH2:15]1)([CH3:34])[CH3:33]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 23155747HCID 23155747, compound

Product 1

HCID 23155692HCID 23155692, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

In a glass tube, 414 mg of 2-[4-(4-quinolin-2-ylpiperazin-1-yl)butyl]-3,1-benzoxazin-4-one as synthesized in above Step 7-15-B, 590 mg of isopropylamine and 5 ml of tetrahydrofuran were hermetically sealed and stirred for an hour at the exterior temperature of 80° C. Cooling the reaction mixture, the solvent was distilled off under reduced pressure, and the resulting residue was purified on silica gel column chromatography (dichloromethane:methanol=10:1) to provide 275 mg (58%) of N-isopropyl-2-[5-(4-quinolin-2-ylpiperazin-1-yl)pentanoylamino]benzamide.

Workup

  1. customwere hermetically sealed
  2. temperatureCooling the reaction mixture
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe resulting residue was purified on silica gel column chromatography (dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-a7e4d0c735a747978f28960af7214929
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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