Diisopropylethylamine → N-(6-(2-(tetrahydro-2H-pyran-4-ylamino)pyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide

HRID 2077572Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:20]=[CH:19][C:11]3[N:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[S:14][C:10]=3[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[NH2:21][CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(N(C(C)C)C(C)C)C>CS(C)=O>[O:25]1[CH2:26][CH2:27][CH:22]([NH:21][C:2]2[N:7]=[C:6]([C:8]3[CH:20]=[CH:19][C:11]4[N:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[S:14][C:10]=4[CH:9]=3)[CH:5]=[CH:4][N:3]=2)[CH2:23][CH2:24]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of N-(6-(2-chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide (0.200 g, 0.7 mmol), 4-aminotetrahydropyran (0.07 ml, 0.7 mmol), N-ethyl-N-isopropylpropan-2-amine (0.2 g, 1 mmol) in DMSO (1 g, 13 mmol) was heated under microwave (CEM) at 150° C. and 130 W (Powermax®& off) for 40 min. Then, the mixture was diluted with 1 ml of DMSO and purified by HPLC (5-50% CH3CN in water) to give a light yellow solid (60 mg) as a TFA salt. MS (ESI pos. ion) Found m/z: 370, (M+H)+.

Workup

custompurified by HPLC (5-50% CH3CN in water)

Sources & evidence

ORD record: ord-9152d1f1049e468f9d555d3c61460823
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928140B2

Reaction notes

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