Diisopropylethylamine → HCID 67040786, compound

HRID 605230Notes

Reaction equation

HRID 605230 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.[F:38][C:39]1[CH:40]=[C:41]([NH2:45])[CH:42]=[N:43][CH:44]=1.C(N(C(C)C)CC)(C)C>O1CCCC1>[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:45][C:41]5[CH:42]=[N:43][CH:44]=[C:39]([F:38])[CH:40]=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

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5744505-Fluoro-3-pyridinamineHCID 86615543HCID 86615543, compound

Product 1

HCID 67040786HCID 67040786, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of Example 19C (259 mg, 0.488 mmol) in anhydrous tetrahydrofuran (5 mL) was treated with the product of Example 224C (60.2 mg, 0.537 mmol) and diisopropylethylamine (0.128 mL, 0.732 mmol), and stirred at room temperature under a nitrogen atmosphere for 15 hours. The solvent was removed by rotary evaporation in vacuo, and the residue was taken up in 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. Trituration with 3% methanol/methylene chloride provided the title compound as a yellow solid (176 mg, 60%).

Workup

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

Sources & evidence

ORD record
ord-cc5dd0d0df734beaa74ef3d661d0e9b8
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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