Isopropylamine → HCID 59518970, compound

HRID 1161879Notes

Reaction equation

HRID 1161879 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[C:17]([O:22][CH3:23])[CH:16]=2)=[CH:13][C:12]2[C:7](=[CH:8][C:9]([Cl:24])=[CH:10][CH:11]=2)[C:6]1=[O:25].[CH3:27][CH:28]([NH2:30])[CH3:29]>CN1C(=O)CCC1>[Cl:24][C:9]1[CH:8]=[C:7]2[C:12]([CH:13]=[C:14]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[C:17]([O:22][CH3:23])[CH:16]=3)[N:5]([CH2:4][C:3]([NH:30][CH:28]([CH3:29])[CH3:27])=[O:2])[C:6]2=[O:25])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6363Isopropylamine2×HCID 59519092HCID 59519092, compound

Product 1

HCID 59518970HCID 59518970, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

[7-Chloro-3-(4-fluoro-3-methoxyphenyl)-1-oxo-1H-isoquinolin-2-yl]acetic acid methyl ester (crude product from the previous experiment) was dissolved in NMP (4 mL). Propan-2-amine (973 mg, 1.402 mL, 16.46 mmol) was added dropwise with stirring and an exotherm was observed. LCMS analysis indicated that the reaction had gone to about 75% completion. Further propan-2-amine (348 mg, 0.5 mL, 5.88 mmol) was added and the reaction mixture heated at reflux temperature for 5 min followed by stirring at room temperature overnight. The resultant precipitate was filtered and washed with diethyl ether (150 mL). This afforded product contaminated with isopropylamine. The solid was dissolved in DCM (50 mL) and washed with water (2×10 mL). The organics were dried (MgSO4) and concentrated to afford 2-[7-chloro-3-(4-fluoro-3-methoxyphenyl)-1-oxo-1H-isoquinolin-2-yl]-N-isopropylacetamide (300 mg, 0.745 mmol).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux temperature for 5 min
  3. stirringby stirring at room temperature overnight
  4. filtrationThe resultant precipitate was filtered
  5. washwashed with diethyl ether (150 mL)
  6. dissolutionThe solid was dissolved in DCM (50 mL)
  7. washwashed with water (2×10 mL)
  8. dry with materialThe organics were dried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-19fccc5e4ef1421486d4d39964285c5b
Source dataset
uspto-grants-2010_10
Patent number
US07820649B2

Reaction notes

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