Diisopropylethylamine → N-((5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-phenyl-1-trityl-1H-imidazol-2-yl)methyl)isoquinolin-6-amine

HRID 2104964Notes

Reaction equation

HRID 2104964 reaction equation
Cl[CH:2]([C:33]1[CH:38]=[C:37]([O:39][CH2:40][CH3:41])[CH:36]=[C:35]([O:42][CH:43]([CH3:45])[CH3:44])[C:34]=1[F:46])[C:3]1[N:4]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.CCN(C(C)C)C(C)C.[NH2:56][C:57]1[CH:58]=[C:59]2[C:64](=[CH:65][CH:66]=1)[CH:63]=[N:62][CH:61]=[CH:60]2>CC#N.CCOC(C)=O>[CH2:40]([O:39][C:37]1[CH:36]=[C:35]([O:42][CH:43]([CH3:44])[CH3:45])[C:34]([F:46])=[C:33]([CH:2]([C:3]2[N:4]([C:14]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:5]=[C:6]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:7]=2)[NH:56][C:57]2[CH:58]=[C:59]3[C:64](=[CH:65][CH:66]=2)[CH:63]=[N:62][CH:61]=[CH:60]3)[CH:38]=1)[CH3:41]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 5889916-AminoisoquinolineHCID 688125412-(chloro(5-ethoxy-2-fluoro-3-isopropoxyphenyl)methyl)-4-phenyl-1-trityl-1H-imidazole

Product 1

HCID 68813003N-((5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-phenyl-1-trityl-1H-imidazol-2-yl)methyl)isoquinolin-6-amineYield 56.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of Intermediate 25.2 (0.054 mmol) in 1 mL CH3CN at rt, were added DIEA (14 μL, 0.082 mmol) and 6-aminoisoquinoline (15.7 mg, 0.109 mmol). The mixture was stirred at rt for 2 h, then was diluted with EtOAc, washed with H2O and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 100% EtOAc/hexanes gradient) to afford 22.5 mg of Intermediate 25.3 as a yellow solid.

Workup

  1. washwashed with H2O and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography (0 to 100% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-d2c8e64d48574d0db3265b211dec1455
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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