4-Toluenesulfonyl chloride → HCID 86600390, compound

HRID 1516054Notes

Reaction equation

HRID 1516054 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.[S:26](Cl)([C:29]1[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=1)(=[O:28])=[O:27].[CH2:37](N(CC)CC)C.CC[CH2:46][CH2:47][CH3:48]>ClCCl.CN(C1C=CN=CC=1)C.O.C(OCC)(=O)C>[C:47]([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:26]([C:29]2[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=2)(=[O:28])=[O:27])=[CH:19][CH:20]=1)([CH3:46])([CH3:48])[CH3:37]

Participants

9

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8003PentaneHCID 8471TriethylamineHCID 596786472-tert-butyl-4-chloro-5-[4-(2-hydroxyethoxymethyl)benzyloxy]-2H-pyridazin-3-one

Product 1

HCID 86600390HCID 86600390, compoundYield 82%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product of Example 5E (200 mg, 0.546 mmol) dissolved in anhydrous dichloromethane (5.50 mL) was added TsCl (125 mg, 0.656 mmol), DMAP (100 mg, 0.819 mmol) and triethylamine (0.091 mL, 0.656 mmol). The reaction mixture continued stirring at room temperature. After 22 hours the reaction mixture was diluted with water. The aqueous layer was separated and extracted with ethyl acetate (3×). All combined organic layers were dried over Na2SO4, filtered, and concentrated to provide an oil. The crude material was purified using silica gel:chromatography (3:2 pentane:ethyl acetate) to provide the desired product (232 mg, 0.447 mmol) in 82% yield. 1H (CDCl37.79, 600 MHz): δ (2H, d, J=8.3 Hz), 7.71 (1H, s), 7.38 (2H, d, J=8.2 Hz), 7.32 (4H, m), 5.30 (2H, s), 4.50 (2H, s), 4.21 (2H, m), 3.69 (2H, m), 2.43 (3H, s), 1.63 (9H, br s); 13C (CDCl3 159.0, 153.7, 144.8, 138.8, 150 MHz): δ 134.4, 133.1, 129.8, 128.1, 128.0, 127.2, 125.1, 118.4, 72.8, 71.7, 69.2, 67.8, 66.4, 27.9, 21.6; HRMS calcd for C25H29ClN2O6: 521.150762, found 521.1503.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (3×)
  3. dry with materialAll combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide an oil
  7. customThe crude material was purified

Sources & evidence

ORD record
ord-715e90e5c87c4d05840f1707666979b5
Source dataset
uspto-grants-2012_07
Patent number
US08226929B2

Reaction notes

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