Water → HCID 86723741, compound

HRID 577514Notes

Reaction equation

HRID 577514 reaction equation
C(O[C:9]1[C:14]([CH2:15][N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[C:19]([CH3:29])[C:20]([C:26](O)=[O:27])=[CH:21][CH:22]=3)[C:17]2=[O:30])=[C:13]([CH3:31])[CH:12]=[C:11]([CH3:32])[N:10]=1)C1C=CC=CC=1.[NH:33]([CH3:35])[CH3:34].Cl.[CH3:37][CH2:38]N(C(C)C)C(C)C.CN(C(ON1N=N[C:56]2[CH:57]=[CH:58][CH:59]=N[C:55]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH2:70]>CN(C=O)C>[CH2:55]([O:70][C:9]1[C:14]([CH2:15][N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[C:19]([CH3:29])[C:20]([C:26]([N:33]([CH3:35])[CH3:34])=[O:27])=[CH:21][CH:22]=3)[C:17]2=[O:30])=[C:13]([CH3:31])[CH:12]=[C:11]([CH3:32])[N:10]=1)[C:56]1[CH:38]=[CH:37][CH:59]=[CH:58][CH:57]=1

Participants

7

Reactant 5

HCID 962WaterHCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86723738HCID 86723738, compound

Product 1

HCID 86723741HCID 86723741, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-methyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-7-carboxylic acid (76e, 120 mg, 0.28 mmol), (CH3)2NH.HCl (34 mg, 0.42 mmol) and DIPEA (181 mg, 1.4 mmol) in DMF (5 mL) under N2 atmosphere was added HATU (214 mg, 0.56 mmol). The mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into water (10 mL) and extracted with EtOAc (3×10 mL). The combined organic layers were washed with H2O (10 mL), brine (2×10 mL), dried over Na2SO4, filtered, and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc=1:1) to give 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-N,N,8-trimethyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-7-carboxamide (76f, 80 mg, 63%) as a colorless gum.

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. washThe combined organic layers were washed with H2O (10 mL), brine (2×10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by column chromatography (petroleum ether/EtOAc=1:1)

Sources & evidence

ORD record
ord-e2dac07b983f4cc39b155bcc985460ab
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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