Dimethyl Sulfoxide → (3-Dimethylaminomethyl-phenyl)-(5-thiophen-3-yl-thiazol-2-yl)-amine

HRID 1713660Notes

Reaction equation

[Si](Br)(C)(C)C.CS(C)=O.[S:10]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]=O)=[CH:11]1.[CH3:18][N:19]([CH2:21][C:22]1[CH:23]=[C:24]([NH:28][C:29]2[S:30]C(C3C=CC=CC=3)=C[N:33]=2)[CH:25]=[CH:26][CH:27]=1)[CH3:20]>CC#N>[CH3:20][N:19]([CH2:21][C:22]1[CH:23]=[C:24]([NH:28][C:29]2[S:30][C:15]([C:12]3[CH:13]=[CH:14][S:10][CH:11]=3)=[CH:16][N:33]=2)[CH:25]=[CH:26][CH:27]=1)[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

Me3SiBr (0.23 mL, 1.75 mmol, 1.1 equiv) and DMSO (0.12 mL, 1.75 mmol, 1.1 equiv) are added sequentially and dropwise to a cold (−35° C.) solution of 3-thiophenylacetaldehyde (200 mg, 1.59 mmol) in CH3CN (3.0 mL), under an argon atmosphere. The resulting mixture is allowed to warm to 0° C., to stir for 50 min, then to warm to room temperature and to stir for 10 min. CH3CN (5.0 mL) is added to the reaction mixture, followed by addition of (3-dimethylaminomethyl-phenyl)-thiourea (Example 2) (333 mg, 1.59 mmol). The reaction mixture is heated to reflux for 1 h, allowed to cool to RT and concentrated in vacuo. MPLC (CH3CN/H2O/TFA) purification affords the title compound: ES-MS: 316.0 [M+H]+; single peak at tR=3.19 min (System 2).

Workup

temperatureto warm to room temperature
stirringto stir for 10 min
temperatureThe reaction mixture is heated
temperatureto reflux for 1 h
temperatureto cool to RT
concentrationconcentrated in vacuo
customMPLC (CH3CN/H2O/TFA) purification

Sources & evidence

ORD record: ord-f219ae6b950c41e48a5f0700701e626c
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795288B2

Reaction notes

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