Potassium Iodide → HCID 54034060, compound

HRID 1267919Notes

Reaction equation

[I-].[K+].[F:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][C:10]=1[F:11])[NH2:7].C(N(CC)C(C)C)(C)C.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([NH:41][C:42](=[O:45])[CH2:43]Cl)[CH:35]=2)[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]>CN(C)C=O.C(OCC)(=O)C.O>[C:21]([O:25][C:26]([N:28]1[CH2:29][CH2:30][N:31]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[C:36]([NH:41][C:42](=[O:45])[CH2:43][NH:7][C:6]3[CH:8]=[CH:9][C:10]([F:11])=[C:4]([F:3])[CH:5]=3)[CH:35]=2)[CH2:32][CH2:33]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

Conditions

Temperature: 90 °C

Procedure

Potassium iodide (10 mg), 3,4-difluoroaniline (0.4 ml), N,N-diisopropyl ethylamine (0.9 ml) and 4-[4-chloro-3-(2-chloro-acetylamino)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (500 mg) were combined in N,N-dimethylformamide (10 ml) and heated at 90° C. for 24 hr. After cooling to room temperature, the reaction was poured into ethyl acetate/water. The organic layer was separated, washed with water (×3) and brine, dried (MgSO4) and concentrated. Purification of the residue by silica gel chromatography (eluting ethyl acetate/iso-hexane (1:2 to 1:1) gave the subtitle product (360 mg).

Workup

temperatureAfter cooling to room temperature
customThe organic layer was separated
washwashed with water (×3) and brine
dry with materialdried (MgSO4)
concentrationconcentrated
customPurification of the residue by silica gel chromatography (
washeluting ethyl acetate/iso-hexane (1:2 to 1:1)

Sources & evidence

ORD record: ord-598e976e19b44fd59cc7a26f2db8cc9c
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06555541B1

Reaction notes

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