71034-40-7 → HCID 59684236, compound

HRID 602275Notes

Reaction equation

HRID 602275 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10](=O)[C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[C:13]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH:12]=3)=[CH:4][C:3]=1[O:29][CH3:30].[NH2:31][CH2:32][C:33]([NH:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34]>>[C:36]([NH:35][C:33](=[O:34])[CH2:32][N:31]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:29][CH3:30])[CH:4]=2)=[CH:17][C:16]2[C:11](=[CH:12][C:13]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)=[CH:14][CH:15]=2)[C:10]1=[O:9])([CH3:39])([CH3:38])[CH3:37]

Participants

3

Reactant 2

HCID 496272271034-40-7HCID 59684264HCID 59684264, compound

Product 1

HCID 59684236HCID 59684236, compoundYield 94%

Conditions

Temperature
120 °C

Procedure

A neat mixture of 3-(4-fluoro-3-methoxyphenyl)-7-(4-methoxybenzyloxy)isochromen-1-one (100 mg, 0.25 mmol) and 2-amino-N-tert-butyl acetamide (INTERMEDIATE I.2) (32 mg, 2.46 mmol) was heated at 120° C. for 3 h. The reaction mixture was cooled and partitioned between ethyl acetate and sat. NH4Cl (aq.). The organic layer was washed with brine (1×20 mL), dried (MgSO4) and concentrated in vacuo to afford N-tert-butyl-2-(3-(4-fluoro-3-methoxyphenyl)-7-(4-methoxybenzyloxy)-1-oxo-1H-isoquinolin-2-yl)acetamide (120 mg, 0.23 mmol, 94%) which was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between ethyl acetate and sat. NH4Cl (aq.)
  3. washThe organic layer was washed with brine (1×20 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aeab2679d0594bc0bdb351a1ea1e4fe7
Source dataset
uspto-grants-2011_03
Patent number
US07906504B2

Reaction notes

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