Diisopropylethylamine → HCID 46832326, compound

HRID 1510290Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[N:17]=[C:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[O:19][C:20]=3[CH3:21])=[O:15])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.F[C:29]1[CH:37]=[CH:36][C:32]([C:33]([OH:35])=[O:34])=[CH:31][N:30]=1.C(N(C(C)C)CC)(C)C>O1CCOCC1>[CH3:21][C:20]1[O:19][C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:17][C:16]=1[C:14]([NH:13][C:10]1[CH:9]=[CH:8][C:7]([CH:4]2[CH2:5][CH2:6][N:1]([C:29]3[CH:37]=[CH:36][C:32]([C:33]([OH:35])=[O:34])=[CH:31][N:30]=3)[CH2:2][CH2:3]2)=[CH:12][CH:11]=1)=[O:15]

Participants

Conditions

Temperature: 175 °C

Procedure

A mixture of 5-methyl-2-phenyl-oxazole-4-carboxylic acid (4-piperidin-4-yl-phenyl)-amide (181 mg, 0.5 mmol) and 6-fluoronicotinic acid (113 mg, 0.8 mmol) in dioxane (2 mL) containing diisopropylethylamine (0.5 mL, 2.7 mmol) was heated in a microwave at 175° C. for 30 minutes. The mixture was evaporated and extracted with ethyl acetate and aqueous citric acid solution. The organic layer was dried over sodium sulfate and solvents were evaporated. The residue was triturated with ethyl acetate and filtered to give a pale pink solid as 4-{4-[(5-methyl-2-phenyl-oxazole-4-carbonyl)-amino]-phenyl}-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carboxylic acid (122.5 mg). LC-MS for C28H26N4O4 (m/e) calcd 482, obsd 483 (M+H). 1H-NMR is consistent with the desired structure.

Workup

customThe mixture was evaporated
extractionextracted with ethyl acetate and aqueous citric acid solution
dry with materialThe organic layer was dried over sodium sulfate and solvents
customwere evaporated
customThe residue was triturated with ethyl acetate
filtrationfiltered

Sources & evidence

ORD record: ord-5c24847f85054594abbb4f551ba747a3
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211914B2

Reaction notes

Loading…