Diisopropylethylamine → HCID 58486976, compound

HRID 874618Notes

Reaction equation

HRID 874618 reaction equation
[CH3:1][C:2]1[C:10]([C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[N:15][CH:16]=2)=[CH:9][C:5]2[N:6]=[CH:7][S:8][C:4]=2[CH:3]=1.[F:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:20]=1[C:21](Cl)=[O:22].CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+].C(Cl)Cl>C(Cl)Cl>[F:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:20]=1[C:21]([NH:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]2[C:2]([CH3:1])=[CH:3][C:4]3[S:8][CH:7]=[N:6][C:5]=3[CH:9]=2)=[CH:16][N:15]=1)=[O:22]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 23716255Sodium bicarbonate methylene chlorideHCID 58486744HCID 58486744, compound

Product 1

HCID 58486976HCID 58486976, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(6-methylbenzothiazol-5-yl)-2-pyridylamine (55) (24 mg, 0.1 mmol) in 2 ml DCM was added 2,6-difluorobenzoyl chloride (25 μl, 0.2 mmol) followed by addition of DIEA (105 μl). The resulting solution was stirred at r.t. for 2 h. The reaction mixture was worked up with aq. NaHCO3/DCM. DCM phase was washed with brine, concentrated to dryness. The residue was dissolved in 2 ml THF/MeOH/H2O (5:4:1) and stirred with 1N NaOH (200 μl) at r.t. for 1 h and then at 50° C. for 2 h before worked up with EA/aq. NaHCO3. Silica gel flash chromatography furnished (2,6-difluorophenyl)-N-[5-(6-methylbenzothiazol-5-yl)(2-pyridyl)]carboxamide (56) (29.6 mg, yield: 77.6%, purity>95%) as white solid.

Workup

  1. washDCM phase was washed with brine
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue was dissolved in 2 ml THF/MeOH/H2O (5:4:1)
  4. stirringstirred with 1N NaOH (200 μl) at r.t. for 1 h
  5. waitat 50° C. for 2 h before worked up with EA/aq

Sources & evidence

ORD record
ord-e700eca182be4dd8b94f479b9174b71e
Source dataset
uspto-grants-2015_03
Patent number
US08980629B2

Reaction notes

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