Hydrochloric Acid → HCID 86689460, compound

HRID 1853694Notes

Reaction equation

HRID 1853694 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]=1[C:17]1[CH:22]=[CH:21][C:20]([CH:23]([CH:33]([CH3:35])[CH3:34])[CH2:24][NH:25]C(=O)OC(C)(C)C)=[CH:19][CH:18]=1.[ClH:36]>CCOCC>[ClH:36].[NH2:25][CH2:24][CH:23]([C:20]1[CH:19]=[CH:18][C:17]([C:4]2[C:5]3[C:6]4[CH:16]=[CH:15][S:14][C:7]=4[C:8](=[O:13])[NH:9][C:10]=3[CH:11]=[CH:12][C:3]=2[O:2][CH3:1])=[CH:22][CH:21]=1)[CH:33]([CH3:34])[CH3:35]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86689450HCID 86689450, compound

Product 1

HCID 86689460HCID 86689460, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Following General Procedure D1, tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methylbutylcarbamate (30 mg, 0.060 mmol) was reacted with HCl in ether (3 mL) to afford the desired product (22 mg, 97%) as an off-white solid; 1H NMR (500 MHz, DMSO-d) δ 7.93 (s, 3H), 7.62 (d, J=5.4 Hz, 1H), 7.53 (d, J=9.1 Hz, 1H), 7.41 (d, J=9.0 Hz, 2H), 7.38-7.33 (m, 1H), 7.24 (d, J=8.2 Hz, 2H), 5.72 (d, J=5.4 Hz, 1H), 3.70 (s, 3H), 3.38-3.26 (m, 2H), 2.87 (dt, J=12.9, 6.3 Hz, 1H), 2.01 (dq, J=13.3, 6.6 Hz, 1H), 0.97 (t, J=7.8 Hz, 3H), 0.82 (t, J=9.9 Hz, 3H); ESI MS m/z 393 [C23H24N2O2S+H]+. HPLC 98.4% (AUC), tR=11.65 min.

Sources & evidence

ORD record
ord-ec70cd63df344d2d9824bbda9cb1f314
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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