HCID 67070560, compound → HCID 67070514, compound

HRID 273161Notes

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)

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-b76ec2f6438d49a5b208301037f08516
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456200B2

Reaction notes

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