N-bromobutanimide → HCID 10073770, compound

HRID 1426066Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[C:16]([O:18][C:19]3[N:20]([CH3:28])[N:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=3)[N:15]=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].C1C(=O)N([Br:36])C(=O)C1>CN(C=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[C:17]([Br:36])=[C:16]([O:18][C:19]3[N:20]([CH3:28])[N:21]=[C:22]([C:24]([F:26])([F:27])[F:25])[CH:23]=3)[N:15]=[CH:14][N:13]=2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-[6-(2-methyl-5-trifluoromethyl-2H-pyrazol-3-yloxy)-pyrimidin-4-yl]-piperidine-4-carboxylic acid ethyl ester (150 mg, 0.37 mmol) and NBS (65 mg, 0.37 mmol) in DMF (3 ml) was stirred at 60° C. for 2 days. The mixture was quenched with sodium thiosulfate, and extracted with ethyl acetate. The combined organic layer was dried with anhydrous sodium sulfate and concentrated in vacuo. Flash chromatography (hexanes:ethyl acetate=3:1) provided compound A19 as a white solid (100 mg, 57%). 1HNMR (CDCl3, 400 MHz) δ 1.28 (t, 3H), 1.78-1.88 (m, 2H), 1.95-2.05 (m, 2H), 2.57-2.62 (m, 1H), 3.17 (t, 2H), 3.81 (s, 3H), 4.18 (q, 2H), 4.22-4.33 (m, 2H), 6.41 (s, 1H), 8.22 (s, 1H). Exact mass calculated for C17H19BrF3N5O3 477.06, found 478.0 (MH+).

Workup

customThe mixture was quenched with sodium thiosulfate
extractionextracted with ethyl acetate
dry with materialThe combined organic layer was dried with anhydrous sodium sulfate
concentrationconcentrated in vacuo
customFlash chromatography (hexanes:ethyl acetate=3:1) provided compound

Sources & evidence

ORD record: ord-108f9a81a1d54c03a734903d55301ee1
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933083B2

Reaction notes

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