Diisopropylethylamine → HCID 59371230, compound

HRID 1510289Notes

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[S:17][CH:18]=[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:20]=3)=[O:15])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.F[C:28]1[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][N:29]=1.C(N(C(C)C)CC)(C)C>O1CCOCC1>[C:21]1([C:19]2[CH:20]=[C:16]([C:14]([NH:13][C:10]3[CH:11]=[CH:12][C:7]([CH:4]4[CH2:5][CH2:6][N:1]([C:28]5[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][N:29]=5)[CH2:2][CH2:3]4)=[CH:8][CH:9]=3)=[O:15])[S:17][CH:18]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 175 °C

Procedure

A mixture of 4-phenyl-thiophene-2-carboxylic acid (4-piperidin-4-yl-phenyl)-amide (181 mg, 0.5 mmol) and 6-fluoronicotinic acid (141 mg, 1 mmol) in dioxane (3 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 (containing THF and methanol) and 0.2N hydrochloric acid. The organic layer was dried and evaporated. The residue was crystallized from methanol and ethyl acetate to give a pale yellow solid as 4-{4-[(4-phenyl-thiophene-2-carbonyl)-amino]-phenyl}-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carboxylic acid (114 mg). LC-MS for C28H25N3O3S (in/e) calcd 483, obsd 484 (M+H). 1H-NMR is consistent with the desired structure.

Workup

customThe mixture was evaporated
extractionextracted with ethyl acetate (containing THF and methanol) and 0.2N hydrochloric acid
customThe organic layer was dried
customevaporated
customThe residue was crystallized from methanol and ethyl acetate

Sources & evidence

ORD record: ord-6b057861908447d79cfa5607d000a090
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211914B2

Reaction notes

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