Triethylamine → HCID 69157507, compound

HRID 1294387Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][N:16]=3)[C:11](=[O:18])[C:10]([C:19](O)=[O:20])=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[F:37][C:38]([F:42])([F:41])[CH2:39][NH2:40]>O1CCCC1>[F:37][C:38]([F:42])([F:41])[CH2:39][NH:40][C:19]([C:10]1[C:11](=[O:18])[C:12]2[C:17](=[N:16][CH:15]=[CH:14][CH:13]=2)[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[CH:9]=1)=[O:20]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 1-(3-bromophenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylic acid from Step 2 (0.1 eq) and triethylamine (3 eq) in tetrahydrofuran (0.08M) at 0° C. was added isobutyl chloroformate (1.8 eq). After stirring at 0° C. for 2 hours, 2,2,2-trifluoroethylamine (5 eq) was added and the mixture was allowed to warm up to room temperature and stirred overnight. The mixture was then partitioned between ethyl acetate and water, the organic phase was dried and evaporated to a solid which was stirred in ether at room temperature for 3 hours and filtered to afford the N-(2,2,2-trifluoroethyl)-1-(3-bromophenyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide as a white solid.

Workup

temperatureto warm up to room temperature
stirringstirred overnight
customThe mixture was then partitioned between ethyl acetate and water
customthe organic phase was dried
customevaporated to a solid which
stirringwas stirred in ether at room temperature for 3 hours
filtrationfiltered

Sources & evidence

ORD record: ord-93bc7877b78640b0ad2a6425df2875c8
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238706B2

Reaction notes

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