Triethylamine → 4-(3-Chloro-4-fluorophenyl)-N-(1-(2-chloropyridin-4-yl)piperidin-4-yl)-6-methylbenzo[d]thiazol-2-amine

HRID 451514Notes

Reaction equation

Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[C:14]([Cl:19])[CH:13]=3)[C:5]=2[N:6]=1.Cl.Cl.[Cl:22][C:23]1[CH:28]=[C:27]([N:29]2[CH2:34][CH2:33][CH:32]([NH2:35])[CH2:31][CH2:30]2)[CH:26]=[CH:25][N:24]=1.C(N(CC)CC)C>CC(N(C)C)=O.ClCCl>[Cl:19][C:14]1[CH:13]=[C:12]([C:7]2[C:5]3[N:6]=[C:2]([NH:35][CH:32]4[CH2:33][CH2:34][N:29]([C:27]5[CH:26]=[CH:25][N:24]=[C:23]([Cl:22])[CH:28]=5)[CH2:30][CH2:31]4)[S:3][C:4]=3[CH:10]=[C:9]([CH3:11])[CH:8]=2)[CH:17]=[CH:16][C:15]=1[F:18]

Participants

Conditions

Temperature: 175 °C

Procedure

To a solution of 2-bromo-4-(3-chloro-4-fluorophenyl)-6-methylbenzo[d]thiazole (0.06 g, 0.2 mmol) in dimethylacetamide (1 mL) was added 1-(2-chloropyridin-4-yl)piperidin-4-amine dihydrochloride (0.05 g, 0.2 mmol) followed by triethylamine (70 L, 0.5 mmol) and the mixture was heated to 175° C. for 1 h in a microwave. The reaction was then diluted with dichloromethane, washed with water, brine, dried with sodium sulfate and concentrated. The product was purified by preparative HPLC to yield the title compound as light yellow solid (0.02 g, 24%).

Workup

washwashed with water, brine
dry with materialdried with sodium sulfate
concentrationconcentrated
customThe product was purified by preparative HPLC

Sources & evidence

ORD record: ord-2a1b8551a62a4ac18b6ecc83247cb0ac
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486967B2

Reaction notes

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