Triethylamine → HCID 56941754, compound

HRID 718310Notes

Reaction equation

Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(N(CC)CC)C.[Cl:25][C:26]1[CH:41]=[CH:40][C:29]([O:30][CH2:31][C:32]([N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)=[O:33])=[CH:28][CH:27]=1>O1CCOCC1>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([O:30][CH2:31][C:32]([N:34]2[CH2:39][CH2:38][N:37]([C:2]3[C:3]4[CH:10]=[C:9]([C:11]5[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=5)[S:8][C:4]=4[N:5]=[CH:6][N:7]=3)[CH2:36][CH2:35]2)=[O:33])=[CH:40][CH:41]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-chloro-6-(4-fluorophenyl)thieno[2,3-d]pyrimidine (20 mg, 0.08 mmol) and triethylamine (42 μl, 0.3 mmol) in dioxane (1 ml) was added 2-(4-chlorophenoxy)-1-(piperazin-1-yl)ethanone (25 mg, 0.1 mmol). The mixture was heated at 60° C. for 2 hours. After cooling down to room temperature, the solvents were removed under reduced pressure. The crude residue was purified by silica gel chromatography (CH2Cl2/MeOH 50:1) to yield the title compound as a white solid (27 mg, 75%).

Workup

temperatureAfter cooling down to room temperature
customthe solvents were removed under reduced pressure
customThe crude residue was purified by silica gel chromatography (CH2Cl2/MeOH 50:1)

Sources & evidence

ORD record: ord-dae9b6eafa42477ba4c3f62dfe57cd45
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193741B2

Reaction notes

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