Nitrogen → HCID 18787662, compound

HRID 1107642Notes

Reaction equation

C([O:8][C:9]1[C:10]2[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][C:11]=2[C:12]2[CH:13]([CH2:25][Cl:26])[CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:16]=2[CH:17]=1)C1C=CC=CC=1.N#N>CCOC(C)=O.C1COCC1.[Pd]>[C:21]([O:20][C:18]([N:15]1[C:16]2[CH:17]=[C:9]([OH:8])[C:10]3[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][C:11]=3[C:12]=2[CH:13]([CH2:25][Cl:26])[CH2:14]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 22 (71.5 mg, 0.159 mmol) and 10% Pd-C (40 mg) in anhydrous EtOAc (5 mL) was degassed with a stream of N2 for 30 s. The resulting mixture was placed under an atmosphere of H2 and stirred at 25° C. for 2.5 h. The mixture was diluted with THF (1 mL) and filtered through Celite (EtOAc wash). The solvent was removed in vacuo. Chromatography (SiO2, 1.5×6 cm, 20% EtOAc-hexane) afforded 23 (57.1 mg, 57.1 mg theoretical, 100%) as a white solid: 1H NMR (CDCl3, 400 MHz) δ8.25 (d, 1H, J=8.7 Hz, C6-H), 7.97 (s, 1H, C9-H), 7.87 (br s, 1H, C4-H), 7.42 (dd, 1H, J=1.5, 8.7 Hz, C7-H), 6.67 (br s, 1H, OH), 4.23 (d, 1H, J=11.4 Hz, C2-H), 4.14 (dd, 1H, J=8.8, 11.8 Hz, C2-H), 3.95 (m, 1H, C1-H), 3.82 (dd, 1H, J=3.2, 11.3 Hz, CHHCl), 3.46 (dd, 1H, J=9.8, 11.2 Hz, CHHCl), 1.59 (s, 9H); 13C NMR (CDCl3, 100 MHz) δ154.2, 153.1, 142.9, 129.4, 127.8, 125.2, 123.2, 122.8, 119.3, 114.7, 111.0, 101.7, 82.5, 53.3, 46.3, 41.3, 28.4; IR (film) vmax 3315 (br), 2964, 2923, 2227, 1676, 1585, 1421, 1369, 1331, 1235, 1141, 729 cm-1 ; FABHRMS (NBA) m/z 358.1076 (M+ +H, C19H19ClN2O3 requires 358.1084).

Workup

filtrationfiltered through Celite (EtOAc wash)
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-072f415bbae54b3d8c1dcc958208cb89
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06060608

Reaction notes

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