Isoxazole-5-carbonyl chloride → HCID 68531620, compound

HRID 2246564Notes

Reaction equation

HRID 2246564 reaction equation
[CH2:1]([C:3]1([O:35][C:36](=[O:45])[O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:8]2[CH:9]=[C:10]3[N:18]([C:19](=[O:20])[C:7]=2[CH2:6][O:5][C:4]1=[O:34])[CH2:17][C:16]1[C:15]([CH2:21][CH2:22][Si:23]([CH2:26][CH2:27][CH2:28][OH:29])([CH3:25])[CH3:24])=[C:14]2[CH:30]=[CH:31][CH:32]=[CH:33][C:13]2=[N:12][C:11]3=1)[CH3:2].[O:46]1[C:50]([C:51](Cl)=[O:52])=[CH:49][CH:48]=[N:47]1>CN(C)C1C=CN=CC=1.ClCCl>[CH2:38]([O:37][C:36]([O:35][C:3]1([CH2:1][CH3:2])[C:8]2[CH:9]=[C:10]3[N:18]([C:19](=[O:20])[C:7]=2[CH2:6][O:5][C:4]1=[O:34])[CH2:17][C:16]1[C:15]([CH2:21][CH2:22][Si:23]([CH3:25])([CH3:24])[CH2:26][CH2:27][CH2:28][O:29][C:51]([C:50]2[O:46][N:47]=[CH:48][CH:49]=2)=[O:52])=[C:14]2[CH:30]=[CH:31][CH:32]=[CH:33][C:13]2=[N:12][C:11]3=1)=[O:45])[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

5

Reactant 2

HCID 2736707Isoxazole-5-carbonyl chlorideHCID 68530161HCID 68530161, compound

Product 1

HCID 68531620HCID 68531620, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
21 °C

Procedure

A mixture of Compound 53 (70 mg, 0.11 mmol), 4-dimethylaminopyridine (30 mg, 0.25 mg), and isoxazole-5-carbonyl chloride (35 μL, 0.22 mmol) in 3.0 mL of dichloromethane was stirred at 21° C. for 5 hours. The reaction was quenched with saturated sodium bicarbonate solution, and aqueous layer was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated to afford a crude product, which was chromatographed to give the desired product.

Workup

  1. customThe reaction was quenched with saturated sodium bicarbonate solution, and aqueous layer
  2. extractionwas extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated
  5. customto afford a crude product, which
  6. customwas chromatographed

Sources & evidence

ORD record
ord-5a734ae61a654afbbd077332f16b5830
Source dataset
uspto-grants-2010_03
Patent number
US07687496B2

Reaction notes

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