Dimethylformamide → HCID 57887230, compound

HRID 1819501Notes

Reaction equation

[CH3:1][N:2]([CH:4]=[O:5])C.[CH3:6][O:7][CH:8]([CH2:25][CH2:26][CH3:27])[CH2:9][CH2:10][C:11]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:12]=1[CH2:13][CH2:14][C:15]1[S:19]C(N)=[N:17][C:16]=12.Br[C:29]1[CH:34]=[C:33]([F:35])[C:32]([CH:36]=[C:37]([CH3:43])[C:38]([O:40][CH2:41][CH3:42])=[O:39])=[C:31]([F:44])[CH:30]=1.C(N(CC)CC)C>O>[F:35][C:33]1[CH:34]=[C:29]([C:4](=[O:5])[NH:2][C:1]2[S:19][C:15]3[CH2:14][CH2:13][C:12]4[C:21](=[CH:22][CH:23]=[CH:24][C:11]=4[CH2:10][CH2:9][CH:8]([O:7][CH3:6])[CH2:25][CH2:26][CH3:27])[C:16]=3[N:17]=2)[CH:30]=[C:31]([F:44])[C:32]=1[CH:36]=[C:37]([CH3:43])[C:38]([O:40][CH2:41][CH3:42])=[O:39]

Participants

Conditions

Temperature: 85 °C

Procedure

To a DMF (25 mL) solution of 4,5-dihydro-6-(3-methyloxyhexyl)naphtho[1,2-d]thiazol-2-ylamine (7) (4.5 g), 3-(4-bromo-2,6-difluorophenyl)-2-methylacrylic acid ethyl ester (3) (4.35 g), and dichlorobistriphenylphosphinepalladium (0.8 g) was added triethylamine (10 mL), and the reaction mixture was stirred under carbon monoxide atomosphere at 85° C. for 16 h. To the reaction mixture was added water, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, and brine, dried over magnesium sulfate, and evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate=4:1) to obtain the compoumd (8) 7.1 g.

Workup

extractionthe reaction mixture was extracted with ethyl acetate
washThe organic layer was washed with water, and brine
dry with materialdried over magnesium sulfate
customevaporated
customThe obtained residue was purified by column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-0cb34d2f356144579a1552d24a6df1bc
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601746B2

Reaction notes

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