Triethylamine → 2-(1-Adamantyloxycarbonyl)-4-(4-fluorophenyl)-5-[4-(Methylsulfonyl)phenyl]-3(2H)-pyridazinone

HRID 1241767Notes

Reaction equation

HRID 1241767 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:24])[NH:10][N:11]=[CH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[C:25]12([O:35][C:36](F)=[O:37])[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]3)[CH2:26]1)[CH2:32]2.CN(C1C=CC=CN=1)C.C(N(CC)CC)C>C(Cl)Cl>[C:25]12([O:35][C:36]([N:10]3[C:9](=[O:24])[C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)=[C:13]([C:14]4[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=4)[CH:12]=[N:11]3)=[O:37])[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]3)[CH2:26]1)[CH2:32]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 644331-Adamantyl fluoroformateHCID 102911854-(4-Fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone

Product 1

HCID 219343132-(1-Adamantyloxycarbonyl)-4-(4-fluorophenyl)-5-[4-(Methylsulfonyl)phenyl]-3(2H)-pyridazinoneYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone, prepared according to the procedure of Example 11 (200 mg, 0.58 mmol) in CH2Cl2 (8 ml) was prepared and stirred. 1-Adamantylfluoroformate (172 mg, 0.87 mmol), dimethylaminopyridine (14 mg, 0.011 mmol) and triethylamine (0.12 ml, 0.87 mmol) were added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with CH2Cl2 (50 ml) and washed with 10% citric acid (50 ml), brine (50 ml) and dried over MgSO4, and concentrated in vacuo. The resulting crude residue was purified using flash chromatography (SiO2, eluting with 15:1 CH2Cl2:diethyl ether) to provide the desired product (yield: 55 mg, 18%). 1H NMR (300 MHz, DMSO-d4) δ 1.66 (bs, 6H), 2.25 (bd, 10H), 3.21 (s, 3H), 7.15 (t, 2H), 7.24 (m, 2H), 7.6 (dd, 2H), 7.88 (d, J=9 Hz, 2H), 8.15 (s, 1H). MS (ESI) m/z 521 (M−H)+. Anal. calc. for C21H15F N2O3S2: C 64.35; H, 5.20; N, 5.36.

Workup

  1. customwas prepared
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. washwashed with 10% citric acid (50 ml), brine (50 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude residue was purified
  7. washflash chromatography (SiO2, eluting with 15:1 CH2Cl2:diethyl ether)

Sources & evidence

ORD record
ord-45eb83dcf6304d51b2d095b773308363
Source dataset
uspto-grants-2006_10
Patent number
US07115591B2

Reaction notes

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