Hydrochloric Acid → (R)-9-(3-Fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one Hydrochloride

HRID 1853697Notes

Reaction equation

HRID 1853697 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]3[C:10]4[CH:24]=[CH:23][S:22][C:11]=4[C:12](=[O:21])[NH:13][C:14]=3[C:15]([CH3:20])=[CH:16][C:17]=2[O:18][CH3:19])[CH:5]=[CH:4][C:3]=1[C@@H:25]([CH3:36])[CH2:26][N:27](C)[C:28](=O)OC(C)(C)C.[ClH:37]>CCOCC>[ClH:37].[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]3[C:10]4[CH:24]=[CH:23][S:22][C:11]=4[C:12](=[O:21])[NH:13][C:14]=3[C:15]([CH3:20])=[CH:16][C:17]=2[O:18][CH3:19])[CH:5]=[CH:4][C:3]=1[C@@H:25]([CH3:36])[CH2:26][NH:27][CH3:28]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86689454HCID 86689454, compound

Product 1

HCID 86689463(R)-9-(3-Fluoro-4-(1-(methylamino)propan-2-yl)phenyl)-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one HydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Following General Procedure D1, (R)-tert-butyl 2-(2-fluoro-4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propyl(methyl)carbamate (50 mg, 0.10 mmol) was reacted with HCl in ether (5 mL) to afford the desired product (35 mg, 85%) as an yellow solid; 1H NMR (500 MHz, CD3OD) δ 7.63 (d, J=5.4 Hz, 1H), 7.53 (dt, J=28.7, 7.8 Hz, 1H), 7.29 (s, 1H), 7.17-7.04 (m, 2H), 6.10 (dd, J=31.6, 5.4 Hz, 1H), 3.75 (s, 3H), 3.68-3.24 (m, 3H), 2.78 (d, J=13.3 Hz, 3H), 2.64 (s, 3H), 1.52 (dd, J=7.0, 3.2 Hz, 3H); ESI MS m/z 411 [C23H23FN2O2S+H]+; HPLC 98.2% (AUC), tR=11.79 min.

Sources & evidence

ORD record
ord-74da8d8a13fc4c93a08044d89f2da575
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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