HCID 69065048, compound → HCID 86623618, compound

HRID 1820994Notes

Reaction equation

HRID 1820994 reaction equation
[F:1][C:2]1([F:36])[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([C:13]3[O:17][N:16]=[C:15]([C:18]4[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:20][C:19]=4[CH3:29])[N:14]=3)=[CH:9][C:8]=2[C:30]#[C:31][Si](C)(C)C)[CH2:3]1>[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:36][C:2]1([F:1])[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([C:13]3[O:17][N:16]=[C:15]([C:18]4[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:20][C:19]=4[CH3:29])[N:14]=3)=[CH:9][C:8]=2[C:30]#[CH:31])[CH2:3]1

Participants

3

Reactant 1

HCID 69065048HCID 69065048, compound

Product 1

HCID 86623618HCID 86623618, compound

Reagents, catalysts & solvents 1

HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

A solution of 5 mg of 3-(4-(5-(6-(3,3-difluoropyrrolidin-1-yl)-5-(trimethylsilyl)ethynylpyridin-3-yl)-1,2,4-oxadiazol-3-yl)-3-methylphenyl)propanoic acid in 200 μL of tetrabutylammonium fluoride (1.0 M in THF) was stirred at rt for 2 h. Purification by HPLC B afforded the title compound: 1HNMR (500 MHz, DMSO) δ 2.48 (m, 4H), 2.86 (t, J=7.3, 2H), 4.09 (t, J=7.3, 2H), 4.24 (t, J=13, 2H), 7.24 (d, J=8.4, 1H), 7.28 (s, 1), 7.92 (d, =8.0, 1H), 8.27 (d, J=2.3, 1H), 8.86 (d, J=2.3, 1H).

Workup

  1. customPurification by HPLC B

Sources & evidence

ORD record
ord-493de637b21e4f64bab0a21263196c01
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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