Triethylamine → HCID 58762454, compound

HRID 858822Notes

Reaction equation

Cl[CH:2]1[C:7](=[O:8])[CH2:6][C:5]([CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([F:19])[F:18])=[C:13]([F:20])[CH:12]=2)[O:4][C:3]1=[O:26].[CH3:27][C:28]1[CH:33]=[C:32]([CH3:34])[N:31]2[N:35]=[C:36]([SH:38])[N:37]=[C:30]2[N:29]=1.C(N(CC)CC)C>CN(C=O)C>[CH:21]1([C:5]2([CH2:9][CH2:10][C:11]3[CH:16]=[CH:15][C:14]([CH:17]([F:19])[F:18])=[C:13]([F:20])[CH:12]=3)[O:4][C:3](=[O:26])[C:2]([S:38][C:36]3[N:37]=[C:30]4[N:29]=[C:28]([CH3:27])[CH:33]=[C:32]([CH3:34])[N:31]4[N:35]=3)=[C:7]([OH:8])[CH2:6]2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 3-chloro-6-cyclopentyl-6-{-[4-(difluoromethyl)-3-fluorophenyl]ethyl}dihydro-2H-pyran-2,4(3H)-dione (200 mg, 0.514 mmol), from Step 1, below, and 5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidine-2-thiol (93 mg, 0.514 mmol) in DMF (4 mL) was treated with triethylamine (52 mg, 0.514 mmol, 1 equiv). The mixture stirred and heated at 55° C. for 4 h. The reaction was cooled to room temperature, and the DMF removed in vacuo. Water and ethyl acetate were added to the resinous material, resulting in the precipitation of a solid. This was filtered, washed with ether, and allowed to air dry, affording 186 mg (68%) of the title product.

Workup

temperatureThe reaction was cooled to room temperature
customthe DMF removed in vacuo
additionWater and ethyl acetate were added to the resinous material
customresulting in the precipitation of a solid
filtrationThis was filtered
washwashed with ether
customto air dry

Sources & evidence

ORD record: ord-5baabe49f50b445f8633858464a3a5d4
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148226B2

Reaction notes

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