Tributylamine → HCID 178448171, compound

HRID 49235Notes

Reaction equation

HRID 49235 reaction equation
[CH:1]([C@H:4]1[O:9][CH2:8][C@H:7]([NH2:10])[CH2:6][O:5]1)([CH3:3])[CH3:2].Cl[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][C:23]2[CH:24]=[N:25][C:26]([OH:29])=[CH:27][CH:28]=2)=[CH:14][N:13]=1.C(N(CCCC)CCCC)CCC>CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH:1]([C@H:4]1[O:9][CH2:8][C@H:7]([NH:10][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH2:22][C:23]3[CH:24]=[N:25][C:26]([OH:29])=[CH:27][CH:28]=3)=[CH:14][N:13]=2)[CH2:6][O:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 7622TributylamineHCID 178448172HCID 178448172, compoundHCID 178515977HCID 178515977, compound

Product 1

HCID 178448171HCID 178448171, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

In a sealed glass bottle under N2-atmosphere, 424 mg (2.92 mmol) of trans 2-isopropyl-[1,3]dioxan-5-ylamine, 396 mg (1.46 mmol) of 1-chloro-4-[(6-hydroxy-pyridin-3-yl)methyl]-isoquinoline (contains 1-iodo derivative) and 2 ml of tributylamine are stirred at 150° C. for 48 h. The resulting mixture is diluted with EtOAc and NaHCO3-solution, the aqueous layer is separated and extracted twice with EtOAc. The organic phases are washed with brine, dried (Na2SO4) and concentrated in vaccuo. “Reversed Phase” medium-pressure chromatography (water/acetonitrile/TFA) yields trans 1-(2-isopropyl-[1,3]dioxan-5-ylamino)-4-[(6-hydroxy-pyridin-3-yl)methyl]-isoquinoline; FAB-MS; (M+H)+=286; HPLC(gradient20-100) tRet=8.6.

Workup

  1. customthe aqueous layer is separated
  2. extractionextracted twice with EtOAc
  3. washThe organic phases are washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vaccuo

Sources & evidence

ORD record
ord-e9ac4aa747d3472587e973ff00ac2a98
Source dataset
uspto-grants-2004_03
Patent number
US06706731B2

Reaction notes

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