Ammonium Chloride → (4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanone

HRID 928824Notes

Reaction equation

HRID 928824 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](I)[CH:10]=2)[N:5]=[C:4]([O:13][CH3:14])[C:3]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1.C([Mg]Cl)(C)C.CON(C)[C:34]([C:36]1[N:40]([CH3:41])[N:39]=[N:38][CH:37]=1)=[O:35].[Cl-].[NH4+]>C1COCC1>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:34]([C:36]3[N:40]([CH3:41])[N:39]=[N:38][CH:37]=3)=[O:35])[CH:10]=2)[N:5]=[C:4]([O:13][CH3:14])[C:3]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 86715652N-Methoxy-N,1-dimethyl-1H-1,2,3-triazole-5-carboxamide2×HCID 867156544-Chloro-6-iodo-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline2×HCID 178418918HCID 178418918, compound

Product 1

HCID 86715636(4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-chloro-6-iodo-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (41.39 g, 86.6 mL, Intermediate 62: step c) in THF (800 mL) was cooled to 4° C., and isopropylmagnesium chloride (44.2 mL, 88.4 mmol, 2 M in THF) was added over 10 min. The mixture was stirred for 20 min and then N-methoxy-N,1-dimethyl-1H-1,2,3-triazole-5-carboxamide (14.74 g, 86.6 mmol, Intermediate 61) in THF (150 mL) was added. After warming to room temperature and stirring for 15 h, a solution of aqueous ammonium chloride (900 mL, 13 wt %) was added. The resulting biphasic mixture was stirred for 15 min. The layers were then separated, and the organic layer was washed with brine (450 mL). The organic layer was diluted with heptane (500 mL) and stirred for 1 h. The resulting suspension was filtered, washed with heptane (100 mL), and dried in a 60° C. vacuum oven to afford the title compound as a white solid.

Workup

  1. stirringstirring for 15 h
  2. stirringThe resulting biphasic mixture was stirred for 15 min
  3. customThe layers were then separated
  4. washthe organic layer was washed with brine (450 mL)
  5. additionThe organic layer was diluted with heptane (500 mL)
  6. stirringstirred for 1 h
  7. filtrationThe resulting suspension was filtered
  8. washwashed with heptane (100 mL)
  9. customdried in a 60° C. vacuum oven

Sources & evidence

ORD record
ord-989958493c2e40ea827538c0c1f71379
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

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