Triethylamine → HCID 49787540, compound

HRID 1020002Notes

Reaction equation

HRID 1020002 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:9]2)=[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[CH:3]=1.[CH:25]1([C:31](Cl)=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(N(CC)CC)C>CC(N(C)C)=O>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:4]1[CH:3]=[C:2]([NH:1][C:31]([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:32])[CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][N:8]([C:12](=[O:17])[C:13]([F:16])([F:14])[F:15])[CH2:9]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 86664382HCID 86664382, compound

Product 1

HCID 49787540HCID 49787540, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1-[7-amino-5-(2-chloro-phenyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2,2,2-trifluoro-ethanone (71 mgs, 0.2 mmoles) was dissolved in anhydrous dimethylacetamide (1 ml) to which was added cyclohexyl carbonyl chloride (40 ul, 0.3 mmoles) followed by triethylamine (41.6 ul, 0.3 mmoles) and the solution flushed with nitrogen and left stirring overnight. The product was purified by semi-preparative C18 HPLC (9.4 mgs, 10.2% yield, 100% pure, CO-AAW00031).

Workup

  1. customthe solution flushed with nitrogen
  2. waitleft
  3. customThe product was purified by semi-preparative C18 HPLC (9.4 mgs, 10.2% yield, 100% pure, CO-AAW00031)

Sources & evidence

ORD record
ord-4e64d5db12f34671a39e497990425ac0
Source dataset
uspto-grants-2014_05
Patent number
US08716302B2

Reaction notes

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