Diisopropylethylamine → HCID 58486960, compound

HRID 2272173Notes

Reaction equation

HRID 2272173 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].[F:12][C:13]([F:31])([F:30])[C:14]1[C:15]([C:23]2[CH:24]=[CH:25][C:26]([NH2:29])=[N:27][CH:28]=2)=[CH:16][C:17]2[C:18]([CH:22]=1)=[N:19][S:20][N:21]=2.CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.ClCCl.O1CCCC1.CO.[OH-].[Li+]>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([NH:29][C:26]1[CH:25]=[CH:24][C:23]([C:15]2[C:14]([C:13]([F:31])([F:30])[F:12])=[CH:22][C:18]3=[N:19][S:20][N:21]=[C:17]3[CH:16]=2)=[CH:28][N:27]=1)=[O:5]

Participants

9

Reactant 3

HCID 81531DiisopropylethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 58487437HCID 58487437, compound

Product 1

HCID 58486960HCID 58486960, compoundYield 76.2%

Reagents, catalysts & solvents 5

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Under an atmosphere of argon, 2,6-difluorobenzoyl chloride (27 mg, 152 μmol) was added to a stirred solution of 20 (30 mg, 101 μmol), Hünig's base (53 μL, 39 mg, 304 μmol), and DMAP (1 mg, 8 μmol) in dichloromethane (500 μL) at room temperature. The reaction was stirred for 10 min. 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 10 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 21 (33.6 mg, 76%) as a solid: LRESIMS m/z 437.1 [M+H]+, calcd. for C19H10F5N4O1S1 437.1.

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-5015c59b285d4d29913568fc0ffa9b84
Source dataset
uspto-grants-2015_09
Patent number
US09120751B2

Reaction notes

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