Selectfluor → HCID 178521028, compound

HRID 931229Notes

Reaction equation

[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[NH:31][C:13]4=[N:14][C:15]([N:18]5[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24]([N:26]6[CH2:30][CH2:29][CH2:28][CH2:27]6)=[O:25])[CH2:19]5)=[CH:16][CH:17]=[C:12]4[N:11]=3)[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1.[B-](F)(F)(F)[F:33].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CN(C)C=O>[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[NH:31][C:13]4=[N:14][C:15]([N:18]5[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24]([N:26]6[CH2:27][CH2:28][CH2:29][CH2:30]6)=[O:25])[CH2:19]5)=[C:16]([F:33])[CH:17]=[C:12]4[N:11]=3)[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

(R)-(1-(2-(2-Cyclopropylpyrimidin-4-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (Example 95, 100 mg, 0.2 mmol) was dissolved in N,N-dimethylformamide. The solution was cooled to 0° C. and Selectfluor (87 mg, 0.2 mmol) was added. The reaction mixture was stirred at 0° C. for 30 min and then at room temperature for 18 h. The reaction mixture was partitioned between ethyl acetate and water. The organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified via HPLC to afford the title compound. MS (ESI+) (M+H) 436.2; HPLC retention time 2.72 min (Method A).

Workup

waitat room temperature for 18 h
customThe reaction mixture was partitioned between ethyl acetate and water
washThe organics were washed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified via HPLC

Sources & evidence

ORD record: ord-ecc0801b6c384dbab85565ac554a30e1
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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