Isobutyryl chloride → HCID 178440412, compound

HRID 892014Notes

Reaction equation

HRID 892014 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH:19]([CH3:31])[CH2:20][C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([OH:30])[CH:28]=4)[NH:23][N:22]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[CH3:41][CH:42]([CH3:46])[C:43](Cl)=[O:44].C(=O)(O)[O-].[Na+]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH:19]([CH3:31])[CH2:20][C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([O:30][C:43](=[O:44])[CH:42]([CH3:46])[CH3:41])[CH:28]=4)[NH:23][N:22]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 62325Isobutyryl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 178440411HCID 178440411, compound

Product 1

HCID 178440412HCID 178440412, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-(9-fluorenylmethoxycarbonylamino)propyl)-1H-indazol-5-ol (0.17 g, 0.41 mmol) and diisopropylehtylamine (0.06 g, 0.50 mmol), in methylene chloride (10 mL) cooled at 0° C. is added 2-methylpropionyl chloride (0.05 g, 0.5 mmol) followed by 4-dimethylaminopyridine (0.05 g, 0.40 mmol). The reaction allowed to warm to room temperature and then is stirred at room temperature. The reaction mixture is added to dilute aqueous sodium bicarbonate and extracted with ether. The combined ether extracts are washed, dried (MgSO4) and concentrated. The residue is purified by chromatography.

Workup

  1. extractionextracted with ether
  2. washThe combined ether extracts are washed
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-304383f822174483bf9c81e3b3515d35
Source dataset
uspto-grants-2006_02
Patent number
US07005443B1

Reaction notes

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