Hydrochloric Acid → HCID 69048748, compound

HRID 749998Notes

Reaction equation

C[O:2][C:3](=[O:28])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]1[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:16][CH:15]=1.Cl>O1CCOCC1>[ClH:27].[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][C:17]2[CH:16]=[CH:15][C:14]([O:13][CH2:12][C@@H:7]3[CH2:8][CH2:9][CH2:10][CH2:11][N:6]3[CH2:5][CH2:4][C:3]([OH:28])=[O:2])=[CH:19][CH:18]=2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To the product from Example 58 (25 mg, 0.0612 mmol) in 1,4-dioxane (1 mL) was added 12N HCl (0.8 mL) and the resulting mixture was stirred at 55° C. for 5 h. The solvent was removed in vacuo to obtain the product as a solid. The oil was triturated with diethyl ether (4 mL) to obtain the title product as a white solid. (19 mg, 73%): MS; m/z 390 (M+H): LCMS (UV) 90%; 1H NMR (400 MHz, DMSO-d6) δ 1.5-1.54 (m, 1H), 1.77-1.79 (m, 4H), 1.95-1.98 (m, 1H) 2.79-2.84 (m, 2H), 3.05-3.1 (m, 1H), 3.37-3.47 (m, 3H), 3.64-3.69 (m, 1H), 4.27-4.29 (m, 2H), 6.94 (d, 2H, J=9.2 Hz), 7.04-7.06 (m, 4H), 7.4 (d, 2H J=8.8 Hz)

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-6b926a89942f4ee4b41b15a809f123e7
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402684B2

Reaction notes

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