4-Toluenesulfonyl chloride → HCID 86600390, compound

HRID 1751842Notes

Reaction equation

HRID 1751842 reaction equation
C([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][O:22][CH2:23][CH2:24][OH:25])=[CH:17][CH:16]=2)[CH:7]=[N:6]1)(C)(C)C.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1.[CH2:37](N(CC)CC)C.CCC[CH2:47][CH2:48][CH3:49]>ClCCl.C(OCC)(=O)C>[C:48]([CH:14]([O:13][C:8]1[CH:7]=[N:6][NH:5][C:10](=[O:11])[C:9]=1[Cl:12])[C:15]1[CH:16]=[CH:17][C:18]([CH2:21][O:22][CH2:23][CH2:24][O:25][S:32]([C:29]2[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=2)(=[O:34])=[O:33])=[CH:19][CH:20]=1)([CH3:47])([CH3:49])[CH3:37]

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8058HexaneHCID 8471TriethylamineHCID 596786472-tert-butyl-4-chloro-5-[4-(2-hydroxyethoxymethyl)benzyloxy]-2H-pyridazin-3-one

Product 1

HCID 86600390HCID 86600390, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product of Example 8E (250 mg, 0.670 mmol) in dichloromethane (7 mL) was added p-toluenesulfonyl chloride (153 mg, 0.805 mmol), N,N-dimethylaminopyridine (DMAP, 98 mg, 0.805 mmol), and triethylamine (140 μL, 1.005 mmol). The reaction was stirred at room temperature overnight under nitrogen atmosphere. Thin layer chromatography (1:1 hexane:ethyl acetate) indicated almost complete consumption of the alcohol. The reaction was concentrated under reduced pressure and the crude material was purified by flash chromatography (2:1 hexane:ethyl acetate to 1:1 hexane:ethyl acetate to 100% ethyl acetate) to recover the starting material (9 mg) and the product (261 mg, 77% yield based on recovered starting material) as a clear oil. 1H NMR (600 MHz, CDCl3): 7.76 (d, 2H, J=8.3 Hz), 7.73 (s, 1H), 7.36 (d, 2H, J=8.1 Hz), 7.29 (m, 4H), 4.47 (s, 2H), 2.40 (s, 3H), 1.61 (s, 9H); 13C NMR (150 MHz, rt, CDCl3): 159.0, 153.8, 145.0, 138.5, 134.4, 133.1, 129.9, 128.1, 128.0, 127.3, 125.2, 118.1, 72.7, 71.0, 37.0, 63.4, 28.0, 21.7.

Workup

  1. customconsumption of the alcohol
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customthe crude material was purified by flash chromatography (2:1 hexane:ethyl acetate to 1:1 hexane:ethyl acetate to 100% ethyl acetate)
  4. customto recover the starting material (9 mg)
  5. customthe product (261 mg, 77% yield based on recovered starting material) as a clear oil

Sources & evidence

ORD record
ord-00cbf02db30f4ea29a44cd473b05d455
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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