Hydrochloric Acid → HCID 69515724, compound

HRID 1178703Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[C:4]=1[CH2:5][S:6][C:7](=[NH:20])[C:8]([C:18]#[N:19])=[C:9]([SH:17])[NH:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.N1C=CC=CC=1.II.[ClH:37]>C(OCC)(=O)C>[ClH:37].[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([NH:10][C:9]2[S:17][N:20]=[C:7]([S:6][CH2:5][C:4]3[C:21]([O:27][CH3:28])=[CH:22][C:23]([O:25][CH3:26])=[CH:24][C:3]=3[O:2][CH3:1])[C:8]=2[C:18]#[N:19])[CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To compound 12 (5.88 g, 14.1 mmol) in ethyl acetate (127 mL) is added pyridine (2.3 mL, 28.3 mmol) at 0° C. A solution of iodine (3.6 g, 14.1 mmol) in ethyl acetate (178 mL) is then added over 2 hours to the reaction. The reaction is then stirred for an additional 3 hours at 0° C. 1N HCl (101.5 mL) is then added and stirred for 5 min. The suspension is then filtered and washed with water to provide 13 (2.53 g, 40%). The mother liquor is basified with saturated aqueous sodium bicarbonate and more ethyl acetate is added (200 mL). The layers are separated and the organic layer is filtered and the mother liquor is concentrated in vacuo. To the resulting solids are added ethyl acetate (183 mL) and 1N HCl (61 mL) and the suspension is stirred for 5 minutes. Filtration provides additional 13 (1.21 g, 19%). 1H NMR (d6 DMSO): δ 11.27 (1H, br. s), 8.72 (1H, d, J=2.1 Hz), 8.49 (1H, dd, J=4.9, 1 Hz), 8.05 (1H, dd, J=8.4, 2.1 Hz), 7.74 (1H, dd, J=8.4, 4.9 Hz), 6.23 (2H, s), 4.35 (2H, s), 3.76 (9H, s).

Workup

stirringstirred for 5 min
filtrationThe suspension is then filtered
washwashed with water

Sources & evidence

ORD record: ord-820f7f9c40594240866dd071856ac25e
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07276602B2

Reaction notes

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