Dimethylformamide → HCID 66599827, compound

HRID 1944167Notes

Reaction equation

OC1C=CC([CH:8]([C:18]([NH:20][C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][CH:30]=2)[CH:27]=[N:26][CH:25]=[CH:24]3)=[O:19])[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=CC=1.[H-].[Na+].Br[CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.CN([CH:45]=[O:46])C>>[CH:27]1[C:28]2[C:23](=[CH:22][C:21]([NH:20][C:18](=[O:19])[CH:8]([C:23]3[CH:22]=[CH:21][CH:30]=[CH:29][C:45]=3[O:46][CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[CH:30][CH:29]=2)[CH:24]=[CH:25][N:26]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 7666Phenethyl bromide

HCID 24758Sodium hydride

HCID 59563693HCID 59563693, compound

Product 1

HCID 66599827HCID 66599827, compound

Conditions

Temperature: -40 °C

Procedure

To tert-butyl 2-(4-hydroxyphenyl)-3-(isoquinolin-6-ylamino)-3-oxopropylcarbamate (E249) in DMF cooled to −35° C. was added NaH and the solution was stirred at −40° C. for 30 min. Then, 2-bromoethylbenzene was added and the solution was warmed and stirred at room temperature for 2 h. The solution was poured into NaHCO3(sat)/EtOAc and further extracted with EtOAc. The combined organics were dried (Na2SO4), filtered, and evaporated. Column chromatography (SiO2, 3-4% MeOH/CH2Cl2) gave pure tert-butyl 3-(isoquinolin-6-ylamino)-3-oxo-2-(phenethoxyphenyl)propylcarbamate (E289).

Workup

temperaturethe solution was warmed
stirringstirred at room temperature for 2 h
extractionfurther extracted with EtOAc
dry with materialThe combined organics were dried (Na2SO4)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-bbb50252f9f245d89813751d0261278e
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394826B2

Reaction notes

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