HCID 67070560, compound → HCID 67070514, compound

HRID 732073Notes

Reaction equation

C(OC(=O)[NH:7][C@H:8]([C:24]1[O:28][N:27]=[C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=2)[N:25]=1)[CH2:9][C:10]1[N:14]([CH:15]2[CH2:17][CH2:16]2)[C:13]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[N:12][N:11]=1)(C)(C)C>C(O)=O>[Cl:35][C:31]1[CH:30]=[C:29]([C:26]2[N:25]=[C:24]([C@@H:8]([NH2:7])[CH2:9][C:10]3[N:14]([CH:15]4[CH2:17][CH2:16]4)[C:13]([C:18]4[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=4)=[N:12][N:11]=3)[O:28][N:27]=2)[CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 50 °C

Procedure

(S)-[1-[3-(3-Chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-2-(4-cyclopropyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-ethyl]-carbamic acid tert-butyl ester (135 mg) was mixed with 96% formic acid (1.3 mL) and heated at 50° C. for 1 h. The reaction mixture was concentrated in vacuo. The residue was quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried with sodium sulfate and concentrated. Purification was performed by flash column silica gel chromatography with 2-3% (2 M ammonia methanol) in dichloromethane to give 106 mg of the title compound as an off-white solid. 1H NMR (CDCl3):d ppm 8.73 (d, 2H), 8.03 (s, 1H), 7.93 (d, 1H), 7.69 (d, 2H), 7.46 (d, 1H), 7.42 (t, 1H), 5.02 (dd, 1H), 3.61 (dd, 1H), 3.49 (dd, 1H), 3.35 (m, 1H), 2.47 (br s, 2H), 1.20 (m, 2H), 0.75 (m, 2H), 0.75 (m, 2H)

Workup

concentrationThe reaction mixture was concentrated in vacuo
customThe residue was quenched with saturated sodium bicarbonate
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried with sodium sulfate
concentrationconcentrated
customPurification

Sources & evidence

ORD record: ord-c1a8fb104f134eb2b1677bebb9228ca5
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585881B2

Reaction notes

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