Hydrochloric Acid → 6-(3-Amino-3-oxopropyl)-2-[3-(4-chlorophenyl)ureido]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide hydrochloride
Reaction equation
[NH2:1][C:2](=[O:28])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]2[C:11]([C:25]([NH2:27])=[O:26])=[C:12]([NH:14][C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)=[O:16])[S:13][C:7]=2[CH2:6]1.Cl>O1CCCC1.CO>[ClH:24].[NH2:1][C:2](=[O:28])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]2[C:11]([C:25]([NH2:27])=[O:26])=[C:12]([NH:14][C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)=[O:16])[S:13][C:7]=2[CH2:6]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of compound D1 (90.0 mg, 0.210 mmol) in tetrahydrofuran (2.5 mL) and methanol (2.5 mL) was added hydrochloride (2 M in diethyl ether, 0.140 mL, 0.280 mmol). After stirring at room temperature for 30 min, the reaction mixture was concentrated under reduced pressure and the resulting residue was triturated with methylene chloride to afford compound D2 as a yellow solid (95 mg, 99%): 1H NMR (500 MHz, DMSO-d6) δ 10.94 (s, 1H), 10.55 (bs, 1H), 10.27 (s, 1H), 7.62 (bs, 1H), 7.55-7.30 (m, 5H), 7.19-7.02 (m, 2H), 4.52-4.48 (m, 1H), 4.28-4.25 (m, 1H), 3.68-3.60 (m, 1H), 3.49-3.42 (m, 3H), 3.13-3.08 (m, 2H), 2.74-2.67 (m, 2H). MS (M+H) 422.
Workup
- concentrationthe reaction mixture was concentrated under reduced pressure
- customthe resulting residue was triturated with methylene chloride
Sources & evidence
- ORD record
- ord-4799af7ea77a4f7f844b5a99c304fff2
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09416141B2
Reaction notes
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