Hydrochloric Acid → 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-N,N-dimethyl-1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide

HRID 577524Notes

Reaction equation

HRID 577524 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH2:15][N:16]2[CH2:25][CH2:24][C:23]3[C:22]([C:26]([OH:28])=O)=[CH:21][C:20]([O:29][CH:30]([CH3:32])[CH3:31])=[C:19]([Cl:33])[C:18]=3[C:17]2=[O:34])=[C:13]([CH3:35])[CH:12]=[C:11]([CH3:36])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:37]([N:39](CC)[CH2:40]C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CNC.Cl>CN(C=O)C.O>[CH2:1]([O:8][C:9]1[C:14]([CH2:15][N:16]2[CH2:25][CH2:24][C:23]3[C:22]([C:26]([N:39]([CH3:40])[CH3:37])=[O:28])=[CH:21][C:20]([O:29][CH:30]([CH3:32])[CH3:31])=[C:19]([Cl:33])[C:18]=3[C:17]2=[O:34])=[C:13]([CH3:35])[CH:12]=[C:11]([CH3:36])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867237502-{[2-(Benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid

Product 1

HCID 867237512-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-N,N-dimethyl-1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-5-carboxamideYield 90.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid (90a, 17 mg, 0.033 mmol) in DMF (1 mL) was added triethylamine (0.023 mL, 0.165 mmol) and HATU (14 mg, 0.035 mmol). The reaction mixture was stirred for 5 minutes, and then dimethylamine.HCl (4.10 mg, 0.050 mmol) was added. The reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with H2O (5 mL) and the solid that precipitated was collected by filtration and dried under vacuum to give 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-N,N-dimethyl-1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide (90b, 16 mg, 89% yield) as a white solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  2. customthe solid that precipitated
  3. filtrationwas collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-d83a7b4702b3453d8359c77c487d2269
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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