Diisopropylethylamine → HCID 54577314, compound

HRID 1036105Notes

Reaction equation

[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](Cl)=[O:5].[Cl:12][C:13]1[C:14]([C:24]2[N: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>CN(C1C=CN=CC=1)C.ClCCl.O1CCCC1.CO.[OH-].[Li+]>[Cl:12][C:13]1[C:14]([C:24]2[N:25]=[CH:26][C:27]([NH:30][C:4](=[O:5])[C:3]3[C:2]([F:1])=[CH:10][CH:9]=[CH:8][C:7]=3[F:11])=[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

Participants

Conditions

Temperature: 60 °C

Procedure

Under an atmosphere of argon, 2,6-difluorobenzoyl chloride (17 mg, 98 μmol) was added to a stirred solution of 117 (14 mg, 49 μmol), Hünig's base (51 μl, 38 mg, 290 μmol), and DMAP (1 mg, 8 μmol) in dichloromethane (780 μL) at room temperature. The reaction was stirred for 0.5 h. The solution was diluted with tetrahydrofuran (1.5 mL), methanol (1 mL) and 1.2 M lithium hydroxide solution (500 μL). The mixture was stirred and heated to 60° C. for 45 min then cooled to room temperature and diluted with dichloromethane (5 mL) and dried with sodium sulfate. The mixture was concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-30% ethyl acetate in hexane) provided 118 (11.5 mg, 55%) as a solid: LRESIMS m/z 426.1 [M+H]+, calcd. for C18H9Cl1F4N3O3 426.0.

Workup

stirringThe mixture was stirred
temperaturethen cooled to room temperature
dry with materialdried with sodium sulfate
concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-23d045c2ccd440e4bf78d288d91f6018
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546403B2

Reaction notes

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