Cyclopropanecarbonyl chloride → HCID 89968212, compound

HRID 1843887Notes

Reaction equation

HRID 1843887 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][C:18]=3[CH3:19])[C:9]2=[O:12])=[CH:4][CH:3]=1.[CH:20]1([C:23](Cl)=[O:24])[CH2:22][CH2:21]1>C1COCC1>[CH3:19][C:18]1[CH:17]=[CH:16][N:15]=[CH:14][C:13]=1[N:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][C:2]([NH:1][C:23]([CH:20]3[CH2:22][CH2:21]3)=[O:24])=[CH:3][CH:4]=2)[C:9]1=[O:12]

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 66803579HCID 66803579, compound

Product 1

HCID 89968212HCID 89968212, compoundYield 14.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using analogous reaction conditions as described in Example 24, 7-amino-2-(4-methyl-pyridin-3-yl)-3,4-dihydro-2H-isoquinolin-1-one (I-25a: 100 mg, 0.3533 mmol) in THF (5 mL) was reacted with cyclopropanecarbonyl chloride (35.5 mL, 0.3886 mmol) and TEA (74.4 mL, 0.5299 mmol) to afford the crude product. Purification by column chromatography on silica gel (80% ethylacetate in hexane), followed by preparative HPLC afforded 16 mg of the product (14% yield).

Workup

  1. customreaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (80% ethylacetate in hexane)

Sources & evidence

ORD record
ord-d354e7eaeeff45598ba638acdcfc866b
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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