Dichloromethane → HCID 54579312, compound

HRID 2272202Notes

Reaction equation

HRID 2272202 reaction equation
F[C:2]1[CH:10]=[CH:9][CH:8]=[C:7](F)[C:3]=1[C:4](Cl)=[O:5].[Cl:12][C:13]1[C:14]([C:24]2[CH:25]=[CH:26][C:27]([NH2:30])=[N:28][CH:29]=2)=[CH:15][C:16]2[O:20][C:19]([F:22])([F:21])[O:18][C:17]=2[CH:23]=1.CCN(C(C)C)C(C)C.[Cl:40]CCl>CN(C1C=CN=CC=1)C.O1CCCC1.CO.[OH-].[Li+]>[Cl:40][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:30][C:27]1[CH:26]=[CH:25][C:24]([C:14]2[C:13]([Cl:12])=[CH:23][C:17]3[O:18][C:19]([F:21])([F:22])[O:20][C:16]=3[CH:15]=2)=[CH:29][N:28]=1)=[O:5]

Participants

9

Reactant 4

HCID 6344Dichloromethane2×HCID 81531DiisopropylethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 58486711HCID 58486711, compound

Product 1

HCID 54579312HCID 54579312, compoundYield 58%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Under an atmosphere of argon, acid 2,6-difluorobenzoyl chloride (16 mg, 92 μmol) was added to a stirred solution of 113 (25 mg, 88 μmol), Hünig's base (46 μL, 34 mg, 260 μmol), and DMAP (1.1 mg, 8.8 μmol) in dichloromethane (440 μL) at room temperature. The reaction was stirred for 0.5 h. The solution was diluted with tetrahydrofuran (500 μL), methanol (200 μL) and 1.2 M lithium hydroxide solution (100 μL). The mixture was stirred and heated to 60° C. for 5 min then cooled to room temperature and diluted with dichloromethane and dried with sodium sulfate. The mixture was concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-50% ethyl acetate in hexane) provided 114 (21.6 mg, 58%) as a solid: LRESIMS m/z 423.3 [M+H]+, calcd. for C19H11Cl2F2N2O3 423.0.

Workup

  1. stirringThe mixture was stirred
  2. temperaturethen cooled to room temperature
  3. dry with materialdried with sodium sulfate
  4. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6d9d8f54dcff4460854a0fed0bf1031e
Source dataset
uspto-grants-2015_09
Patent number
US09120751B2

Reaction notes

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