5-Methylisoxazole-3-carbonyl chloride → HCID 86601375, compound

HRID 857289Notes

Reaction equation

HRID 857289 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][C:13]2[CH:14]=[C:15]([C:19]3[CH:20]=[C:21]([C:29]([CH3:33])([CH3:32])[C:30]#[N:31])[CH:22]=[C:23]4[C:28]=3[N:27]=[CH:26][CH:25]=[CH:24]4)[CH:16]=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)(=O)=O.[CH3:34][C:35]1[O:39][N:38]=[C:37]([C:40](Cl)=[O:41])[CH:36]=1>N1C=CC=CC=1.C([O-])(O)=O.[Na+]>[C:30]([C:29]([CH3:33])([CH3:32])[C:21]1[CH:22]=[C:23]2[C:28](=[C:19]([C:15]3[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=3)[CH2:12][N:11]([C:8]3[CH:9]=[CH:10][C:5]([S:2][CH3:1])=[CH:6][CH:7]=3)[C:40]([C:37]3[CH:36]=[C:35]([CH3:34])[O:39][N:38]=3)=[O:41])[CH:20]=1)[N:27]=[CH:26][CH:25]=[CH:24]2)#[N:31]

Participants

5

Reactant 2

HCID 27368945-Methylisoxazole-3-carbonyl chlorideHCID 21865597HCID 21865597, compound

Product 1

HCID 86601375HCID 86601375, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of the amine from Step 1 (1.0 eq) and 5-methyl-isoxazole-3-carbonyl chloride (1.8 eq) in pyridine (0.35M) was stirred for 12 h, poured in saturated aqueous NaHCO3 and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 3:2) afforded the desired compound as a foam.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-605eb3f88fe044c7801d035a915a5603
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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