Diisopropylethylamine → HCID 67040170, compound

HRID 605196Notes

Reaction equation

HRID 605196 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:37])[NH:17][C:18]3[CH:23]=[CH:22][C:21]([S:24][C:25]4[CH:30]=[CH:29][C:28]([C:31](Cl)=[O:32])=[CH:27][C:26]=4[N+:34]([O-:36])=[O:35])=[CH:20][CH:19]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.[NH2:39][C:40]1[S:44][N:43]=[C:42]([CH3:45])[CH:41]=1.C(N(C(C)C)CC)(C)C>O1CCCC1.C(OCC)(=O)C>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:37])[NH:17][C:18]3[CH:23]=[CH:22][C:21]([S:24][C:25]4[CH:30]=[CH:29][C:28]([C:31](=[O:32])[NH:39][C:40]5[S:44][N:43]=[C:42]([CH3:45])[CH:41]=5)=[CH:27][C:26]=4[N+:34]([O-:36])=[O:35])=[CH:20][CH:19]=3)[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

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27239183-Methylisothiazol-5-ylamine hydrochlorideHCID 86615543HCID 86615543, compound

Product 1

HCID 67040170HCID 67040170, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product of Example 19C (290 mg, 0.546 mmol) in anhydrous tetrahydrofuran (5 mL) was treated with 5-amino-3-methylisothiazole hydrochloride (90.5 mg, 0.6008 mmol) and diisopropylethylamine (0.238 mL, 1.365 mmol), and stirred at room temperature under a nitrogen atmosphere for 18 hours. The reaction was diluted with ethyl acetate (100 mL) and washed with saturated aqueous sodium bicarbonate (25 mL), water (2×25 mL), and brine (25 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to provide the title compound (202 mg, 61%).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (25 mL), water (2×25 mL), and brine (25 mL)
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4b2a2305f8974755add28f6cd3d5822c
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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