Diisopropylethylamine → HCID 86662867, compound

HRID 1910889Notes

Reaction equation

HRID 1910889 reaction equation
[NH2:1][C@H:2]([C:4]1[N:5]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:6](=[O:20])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][C:8]=2[C:14]1[CH:15]=[N:16][N:17]([CH3:19])[CH:18]=1)[CH3:3].[Cl:27][C:28]1[N:33]=[C:32](Cl)[C:31]([I:35])=[CH:30][N:29]=1.CCN(C(C)C)C(C)C>C(O)CCC>[Cl:27][C:28]1[N:33]=[C:32]([NH:1][C@H:2]([C:4]2[N:5]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:6](=[O:20])[C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][C:8]=3[C:14]2[CH:15]=[N:16][N:17]([CH3:19])[CH:18]=2)[CH3:3])[C:31]([I:35])=[CH:30][N:29]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2634382,4-Dichloro-5-iodopyrimidineHCID 66608768HCID 66608768, compound

Product 1

HCID 86662867HCID 86662867, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

(S)-3-(1-Aminoethyl)-8-(1-methyl-1H-pyrazol-4-yl)-2-phenylisoquinolin-1(2H)-one (63) (570 mg, 1.66 mmol), 2,4-dichloro-5-iodopyrimidine (455 mg, 1.66 mmol) and DIEA (0.27 mL, 1.66 mmol) were dissolved in n-butanol (12 mL) in a sealed tube, and the resulting mixture was stirred at 100° C. for 16 h. The mixture was allowed to cool to RT, quenched with water and extracted with ethyl acetate (150 mL×2). The combined organic layers were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to afford the product (S)-3-(1-((2-chloro-5-iodopyrimidin-4-yl)amino)ethyl)-8-(1-methyl-1H-pyrazol-4-yl)-2-phenylisoquinolin-1(2H)-one (64) as an oil. The product obtained was used in the next step without purification. ESI-MS m/z: 583.0 [M+H]+.

Workup

  1. temperatureto cool to RT
  2. customquenched with water
  3. extractionextracted with ethyl acetate (150 mL×2)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cf76ad340dd6463dbfc51cab6c8e4ce0
Source dataset
uspto-grants-2013_12
Patent number
US08604032B2

Reaction notes

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