Dimethylcarbamoyl Chloride → 2-(Trimethylsilyl)ethyl 4-{4-[(dimethylcarbamoyl)oxy]phenyl}isoquinoline-6-carboxylate

HRID 1959955Notes

Reaction equation

HRID 1959955 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])=[O:19])[CH:16]=3)[CH:11]=[N:10][CH:9]=2)=[CH:4][CH:3]=1.FC(F)(F)S(OC1C2C(=CC=C(C(OCC[Si](C)(C)C)=O)C=2)C=NC=1)(=O)=O.C(N(CC)CC)C.[CH3:61][N:62]([CH3:66])[C:63](Cl)=[O:64]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:61][N:62]([CH3:66])[C:63]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])=[O:19])[CH:16]=3)[CH:11]=[N:10][CH:9]=2)=[CH:6][CH:7]=1)=[O:64]

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 584957602-(Trimethylsilyl)ethyl 4-{[(trifluoromethyl)sulfonyl]oxy}isoquinoline-6-carboxylateHCID 667305282-(Trimethylsilyl)ethyl 4-(4-hydroxyphenyl)isoquinoline-6-carboxylate

Product 1

HCID 667303722-(Trimethylsilyl)ethyl 4-{4-[(dimethylcarbamoyl)oxy]phenyl}isoquinoline-6-carboxylateYield 93.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Into dichloromethane (6.5 mL), 2-(trimethylsilyl)ethyl 4-(4-hydroxyphenyl)isoquinoline-6-carboxylate (234 mg, 0.64 mmol) synthesized from 2-(trimethylsilyl)ethyl 4-{[(trifluoromethyl)sulfonyl]oxy}isoquinoline-6-carboxylate by the same method as in Example 8 (8a) was dissolved, to which triethylamine (178 μL, 1.28 mmol), 4-dimethylaminopyridine (23 mg, 0.19 mmol) and N,N-dimethylcarbamoyl chloride (88 μL, 0.96 mmol) were added, followed by stirring at room temperature for three hours. The resulting reaction liquid was concentrated under reduced pressure and the residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-50:50, V/V) to give the desired title compound (260 mg, yield 93%).

Workup

  1. additionwere added
  2. customThe resulting reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. customthe residue thus obtained
  5. customwas purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-50:50, V/V)

Sources & evidence

ORD record
ord-6d52655e74814895b97a43a611935b28
Source dataset
uspto-grants-2013_04
Patent number
US08410273B2

Reaction notes

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