Thionyl Chloride → HCID 86626538, compound

HRID 1698060Notes

Reaction equation

Cl.[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]3[S:16][C:17]4[CH:23]=[C:22]([C:24]([OH:26])=O)[CH:21]=[CH:20][C:18]=4[N:19]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.S(Cl)([Cl:29])=O>CN(C=O)C>[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]3[S:16][C:17]4[CH:23]=[C:22]([C:24]([Cl:29])=[O:26])[CH:21]=[CH:20][C:18]=4[N:19]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1

Participants

Conditions

Temperature: 70 °C

Procedure

2-[6-(4-Methylpiperazin-1-yl)pyridin-3-yl]-1,3-benzothiazole-6-carboxylic acid hydrochloride acid (46 mg, 0.12 mmol) was added to thionyl chloride (3 mL), followed by 3 drops DMF, before heating at 70° C. o.n. The solvent was thereafter evaporated in vacuo and once with toluene to give crude 2-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]-1,3-benzothiazole-6-carbonyl chloride. Ammonium hydroxide (conc., 3 mL) was added dropwise to this crude product and the mixture was thereafter stirred for 1 h at r.t. The r.m. was extracted twice with DCM, dried (Na2SO4), and evaporated in vacuo. The obtained residue was purified by prep. HPLC to give the title compound (7 mg) as a light yellow solid. 1H NMR δ 8.81 (d, 1H) 8.58 (s, 1H) 8.16 (dd, 1H) 8.07 (br. s., 1H) 7.99 (s, 2H) 7.45 (br. s., 1H) 7.00 (d, 1H) 3.61-3.71 (m, 4H) 2.37-2.46 (m, 4H) 2.23 (s, 3H) 1.89 (s, 3H); MS m/z (M+H) 354.

Workup

customThe solvent was thereafter evaporated in vacuo and once with toluene

Sources & evidence

ORD record: ord-1d533ae0d73843ceb73e1220b08bfa13
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163928B2

Reaction notes

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