Trifluoroacetic acid → HCID 67339276, compound

HRID 2092313Notes

Reaction equation

HRID 2092313 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([N+:13]([O-])=O)[C:8]([CH3:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:16][C:17]1[S:18][C:19]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][C:20]=2[N:21]=1.C(O)(C(F)(F)F)=O>C(O)(C)C>[ClH:1].[CH3:12][C:8]1[CH:9]=[CH:10][C:11]2[C:2]([NH:26][C:23]3[CH:24]=[CH:25][C:19]4[S:18][C:17]([CH3:16])=[N:21][C:20]=4[CH:22]=3)=[N:3][CH:4]=[CH:5][C:6]=2[C:7]=1[NH2:13]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 362295-Benzothiazolamine, 2-methyl-HCID 226222211-Chloro-6-methyl-5-nitroisoquinoline

Product 1

HCID 67339276HCID 67339276, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Alternative preparation to Example 5: To a round bottom flask fitted with reflux condenser was added 1-chloro-6-methyl-5-nitroisoquinoline (13.0 g, 50 mmol), and 2-methyl-5-benzothiazolamine (8.63 g, 52.5 mmol). Nitrogen atmosphere was applied, and the mixture was treated with isopropanol (111 mL). The reaction vessel contents were stirred to obtain a slurry. TFA (11.35 mL, 150 mmol) was then added slowly and the contents of the flask were heated to reflux. The reaction was held at reflux for 17 h, then removed from heat. The reaction mixture was filtered on a fritted funnel at room temperature. The solid was reslurried in refluxing isopropanol (222 mL) for 18 h. The slurry was then cooled to room temperature and filtered. The resulting yellow solid was then dried under vacuum at 55° C. overnight to 17.77 g 6-methyl-N1-(2-methylbenzo[d]thiazol-5-yl)isoquinoline-1,5-diamine hydrochloride (91% yield). MS (M+H)+ 351.

Workup

  1. customAlternative preparation to Example 5
  2. customTo a round bottom flask fitted
  3. temperaturewith reflux condenser
  4. customto obtain a slurry
  5. temperaturethe contents of the flask were heated to reflux
  6. temperatureat reflux for 17 h
  7. customremoved
  8. temperaturefrom heat
  9. filtrationThe reaction mixture was filtered on a fritted funnel at room temperature
  10. temperaturein refluxing isopropanol (222 mL) for 18 h
  11. filtrationfiltered

Sources & evidence

ORD record
ord-f3629b0e08414bcc84f35a08bcdec7c5
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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