Hydrochloric Acid → HCID 86689470, compound

HRID 1853707Notes

Reaction equation

HRID 1853707 reaction equation
[CH:1]1([CH:6]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:23]4[C:24]5[CH:37]=[CH:36][S:35][C:25]=5[C:26](=[O:34])[NH:27][C:28]=4[CH:29]=[CH:30][C:31]=3[O:32][CH3:33])=[CH:18][CH:17]=2)[CH2:7][NH:8]C(=O)OC(C)(C)C)[CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:38]>CCOCC>[ClH:38].[NH2:8][CH2:7][CH:6]([C:16]1[CH:17]=[CH:18][C:19]([C:22]2[C:23]3[C:24]4[CH:37]=[CH:36][S:35][C:25]=4[C:26](=[O:34])[NH:27][C:28]=3[CH:29]=[CH:30][C:31]=2[O:32][CH3:33])=[CH:20][CH:21]=1)[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86689458HCID 86689458, compound

Product 1

HCID 86689470HCID 86689470, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Following General Procedure D, tert-butyl 2-cyclopentyl-2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate (50 mg, 0.10 mmol) was reacted with HCl in ether (5 mL) to afford the desired product (29 mg, 69%) as an off-white solid: ESI MS m/z 419 [C25H26N2O2S+H]+; 1H NMR (500 MHz, DMSO-d6) δ 7.59 (d, J=5.4 Hz, 1H), 7.59 (d, J=5.4 Hz, 1H), 7.54 (d, J=9.0 Hz, 1H), 7.54 (d, J=9.0 Hz, 1H), 7.48 (d, J=7.9 Hz, 1H), 7.48 (d, J=7.9 Hz, 1H), 7.44-7.36 (m, 2H), 7.45-7.35 (m, 2H), 7.28-7.19 (m, 2H), 7.28-7.19 (m, 2H), 5.72 (d, J=5.4 Hz, 1H), 5.72 (d, J=5.4 Hz, 1H), 3.70 (s, 3H), 3.33-3.20 (m, 2H), 2.84 (td, J=9.2, 6.0 Hz, 1H), 2.20-2.03 (m, 1H), 1.98-1.84 (m, 1H), 1.76-1.35 (m, 5H), 1.28 (dq, J=18.0, 8.9 Hz, 1H), 1.18-1.02 (m, 1H). HPLC >99% (AUC), tR=12.45 min.

Sources & evidence

ORD record
ord-6706cca8d1bd463ea5bbbc3c431e1cae
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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