Hydrochloric Acid → HCID 70563065, compound

HRID 1427268Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the product from step D (15 mg, 0.028 mmol, enantiomer A) in EtOH (2 mL) was added 2N HCl (0.5 mL). The mixture was stirred at 50° C. overnight. The volatile was removed under reduced pressure and the residue was purified by Combiflash (Mobile phase: MeOH/H2O (0.08% of NH4HCO3) to obtain the title compound. LC/MS m/z=412.1 [M+H]+. 1H NMR (400 MHz, CDC13) δ• •7.53 (d, J=3.6 Hz, 1H), 7.33 (d, J=8.8 Hz, 2H), 7.17 (d, J=8.0 Hz, 1H), 7.12 (d, J=8.4 Hz, 2H), 7.01 (t, J=8.0 Hz, 1H), 6.73 (d, J=8.4 Hz, 1H), 6.70 (d, J=3.6 Hz, 1H), 6.62 (br, 1H), 3.04 (s, 3H), 2.80-2.76 (m, 1H), 2.52-2.48 (m, 1H), 1.05 (t, J=7.2 Hz, 3H).

Workup

customThe volatile was removed under reduced pressure
customthe residue was purified by Combiflash (Mobile phase

Sources & evidence

ORD record: ord-850535f68b9b49a4b294a1a8122b3c8c
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933113B2

Reaction notes

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