Isopropanol → 3-(4-(6-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-1,3,5-triazin-2-ylamino)-2-methylbenzamide

HRID 522886Notes

Reaction equation

HRID 522886 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:12]1[N:17]=[C:16](Cl)[N:15]=[CH:14][N:13]=1)[CH2:6][CH2:5]2.[NH2:19][C:20]1[C:21]([CH3:29])=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23]([NH2:25])=[O:24].C(N(C(C)C)C(C)C)C.CC(O)C>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([C:12]1[N:13]=[CH:14][N:15]=[C:16]([NH:19][C:20]3[C:21]([CH3:29])=[C:22]([CH:26]=[CH:27][CH:28]=3)[C:23]([NH2:25])=[O:24])[N:17]=1)[CH2:6][CH2:5]2

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 81531DiisopropylethylamineHCID 164957733-Amino-2-methylbenzamideHCID 772313486-Bromo-2-(4-chloro-1,3,5-triazin-2-yl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 673770373-(4-(6-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-1,3,5-triazin-2-ylamino)-2-methylbenzamideYield 25.1%

Conditions

Temperature
95 °C

Procedure

To a vial charged with 6-bromo-2-(4-chloro-1,3,5-triazin-2-yl)-1,2,3,4-tetrahydroisoquinoline (163 mg, 499 μmol) and 3-amino-2-methylbenzamide (75 mg, 499 μmol) was added N-ethyl-N-isopropylpropan-2-amine (174 μl, 999 μmol) and propan-2-ol (1665 μl, 499 μmol). The vial was sealed and heated to 95° C. overnight. The product was purified by reverse phase liquid chromatography using TFA as a modifier. Fractions containing the product were combined and neutralized with saturated NaHCO3 (35 mL). The product was extracted with DCM (3×30 mL). The organics were separated, dried over Na2SO4, and filtered to afford 3-(4-(6-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-1,3,5-triazin-2-ylamino)-2-methylbenzamide (55 mg, 25%) as a white solid upon drying.

Workup

  1. customThe vial was sealed
  2. customThe product was purified by reverse phase liquid chromatography
  3. additionFractions containing the product
  4. extractionThe product was extracted with DCM (3×30 mL)
  5. customThe organics were separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-27c869f11ec84fb7aceaef18044197fc
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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