Pyridine → Hydrochloric Acid

HRID 1796500Notes

Reaction equation

HRID 1796500 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([Cl:17])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH3:27])=[CH:21][CH:20]=2)[CH2:3][CH2:2]1.[CH2:28]([NH2:30])[CH3:29].N1C=CC=CC=1>C(Cl)Cl.C(OCC)C>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([NH:30][CH2:28][CH3:29])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH3:27])=[CH:21][CH:20]=2)[CH2:3][CH2:2]1.[ClH:17]

Participants

7

Reactant 3

HCID 1049PyridineHCID 6341EthylamineHCID 22181266HCID 22181266, compound

Product 2

HCID 313Hydrochloric AcidHCID 22181311HCID 22181311, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Following general procedure 36B: Used 1-(cyclopropylmethyl)-2-(4-ethoxybenzyl)-1H-benzimidazole-5-sulfonyl chloride (from 0.2 mmol of aniline precursor), ethyl amine (2M solution in THF, 0.4 mmol) and pyridine (0.5 mL) in CH2Cl2 (4 mL). The resulting mixture was stirred at room temperature overnight. Isolated the desired product as the HCl salt after column chromatography and treatment with 1 M HCl solution in diethyl ether (61 mg, 87%). 1H NMR (400 MHz, CD3OD): δ 8.28 (s, 1H), 7.78 (d, J=8.0 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.15 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.8 Hz, 2H), 4.32 (s, 2H), 4.02–3.93 (m, 4H), 3.06–2.98 (m, 2H), 1.38 (t, J=7.6 Hz, 3H), 1.10 (t, J=8.0 Hz, 3H), 1.07–1.00 (m, 1H), 0.55–0.52 (m, 2H), 0.30–0.24 (m, 2H). MS (ESI) (M+H)+=414. Anal. Calcd for C12H27N3O3S.1.1HCl: C, 58.25; H, 6.24; N, 9.26. Found: C, 58.19; H, 6.73; N, 8.62.

Sources & evidence

ORD record
ord-b123946b45e3444db50460c2e6e78378
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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