Water → HCID 59536367, compound

HRID 445314Notes

Reaction equation

HRID 445314 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14][NH:13]2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].CCN(C(C)C)C(C)C.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([N:37]=[C:38]=[O:39])[CH:32]=1.O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14][N:13]2[C:38]([NH:37][C:33]2[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=2)=[O:39])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:9])[F:10]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27604933-IsocyanatopyridineHCID 59536303HCID 59536303, compound

Product 1

HCID 59536367HCID 59536367, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3-fluoro-4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (0.1500 g, 0.508 mmol, Example 71 Step 3) was dissolved in 3 mL CH2Cl2 and DIEA (0.0884 mL, 0.508 mmol) and 3-pyridyl isocyanate (0.0732 g, 0.610 mmol) were added at RT. The mixture was stirred over night and hydrolyzed with 2 mL water. The reaction was extracted 3 times with EtOAc (3×20 mL), dried over MgSO4 and evaporated. The crude product was purified via glass column chromatography providing 1-(3-fluoro-4-(trifluoromethyl)phenyl)-N-(pyridin-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide as a white solid. MS (ESI, positive ion) m/z: 416.0 (M+H). The majority of the material was submitted for chiral purification (SFC):

Workup

  1. extractionThe reaction was extracted 3 times with EtOAc (3×20 mL)
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe crude product was purified via glass column chromatography

Sources & evidence

ORD record
ord-09ce04996f184d08b352f63bbfa50314
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

Loading…