Triethylamine → HCID 11744184, compound

HRID 2113954Notes

Reaction equation

[CH3:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[N:9]=2)=[C:5]([CH3:7])[N:6]=1.CCN(CC)CC.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[CH3:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:16]=[CH:17][C:18]([N:21]4[CH2:22][CH2:23][N:24]([S:35]([CH3:34])(=[O:37])=[O:36])[CH2:25][CH2:26]4)=[CH:19][CH:20]=3)[N:9]=2)=[C:5]([CH3:7])[N:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of [4-(2,4-dimethyl-thiazol-5-yl)-pyrimidin-2-yl]-(4-piperazin-1-yl-phenyl)-amine (86 mg, 0.23 mmol) in anhydrous CH2Cl2 (2 mL) was added Et3N (39 μL, 0.28 mmol). After cooling to 0° C., methanesulfonyl chloride (22 μL, 0.28 mmol) was added dropwise. After 15 min stirring, the reaction mixture was warmed to room temperature and stirring was continued for 18 h. After evaporation, the residue was purified by SiO2 chromatography (98:2 to 95:5 EtOAc/2 M NH3 in MeOH) to afford the title compound (61 mg) as a yellow solid. 1H-NMR (CDCl3) δ: 2.69 (s, 3H, CH3), 2.71 (s, 3H, CH3), 2.84 (s, 3H, CH3), 3.26 (t, 4H, J=5.1 Hz, CH2), 3.41 (t, 4H, J=5.1 Hz, CH2), 6.91 (d, 1H, J=5.1 Hz, pyrimidinyl-H), 6.98 (d, 2H, J=8.8 Hz, Ph-H), 7.10 (br. s, 1H, NH), 7.56 (d, 2H, J=8.8 Hz, Ph-H), 8.30 (d, 1H, J=5.1 Hz, pyrimidinyl-H). MS (ESI+) m/z 446 (C20H24N6O2S2 requires 444.6).

Workup

temperaturethe reaction mixture was warmed to room temperature
stirringstirring
waitwas continued for 18 h
customAfter evaporation
customthe residue was purified by SiO2 chromatography (98:2 to 95:5 EtOAc/2 M NH3 in MeOH)

Sources & evidence

ORD record: ord-a252dc54a0ee4fc0b0d1b67630e6b5a1
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432260B2

Reaction notes

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