Triethylamine → HCID 49787507, compound

HRID 1020001Notes

Reaction equation

HRID 1020001 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.[C:25](Cl)(=[O:30])[CH2:26][CH2:27][CH2:28][CH3:29].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:25](=[O:30])[CH2:26][CH2:27][CH2:28][CH3:29])[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 61186Valeryl chlorideHCID 86664382HCID 86664382, compound

Product 1

HCID 49787507HCID 49787507, compoundYield 13.1%

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 valeryl chloride (36 ul, 0.3 mmoles) and finally triethylamine (41.6 ul, 0.3 mmoles). The vial was flushed with nitrogen and stirred at room temperature overnight. The product was twice purified by semi-preparative C18 HPLC (11.5 mgs, 13.1% yield, 94% pure, CO-AAW00030).

Workup

  1. customThe vial was flushed with nitrogen
  2. customThe product was twice purified by semi-preparative C18 HPLC (11.5 mgs, 13.1% yield, 94% pure, CO-AAW00030)

Sources & evidence

ORD record
ord-82da4f1d8e5e4982830515b8d34cda00
Source dataset
uspto-grants-2014_05
Patent number
US08716302B2

Reaction notes

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