Triethylamine → HCID 58762454, compound

HRID 1453278Notes

Reaction equation

HRID 1453278 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

5

Reactant 3

HCID 8471TriethylamineHCID 58762386HCID 58762386, compoundHCID 178426287HCID 178426287, compound

Product 1

HCID 58762454HCID 58762454, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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. 1H NMR (DMF-d7) δ 1.81-2.00 (m, 8H) 2.56-2.62 (m, 2H) 2.71 (s, 3H) 2.76 (s, 3H) 2.80 (m, 1H) 3.07(m, 2H) 3.14 (d, J=6 Hz, 1H) 3.32 (d, J=18 Hz, 1H) 7.40 (t, J=57 Hz, 1H), 7.24 (s, 1H) 7.66 (m, 2H) 7.84 (m, 1H,). MS (APCI) calcd for C26H27F3O3S: 532.58; MS found; (M+H+) 533.1. Anal. Calc'd for C26H27F3O3S: C, 58.64; H, 5.11; N, 10.52; S, 6.02. Found: C, 58.26, 58.33; H, 5.25, 5.14; N, 10.69, 10.61; S, 5.78, 5.79.

Workup

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

Sources & evidence

ORD record
ord-b329da5377a548488e4f74e356ffae97
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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