Tetrabutylammonium Fluoride → HCID 178449203, compound

HRID 2280425Notes

Reaction equation

HRID 2280425 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:20]=[C:19]([NH:21]/[C:22](/[NH:34][CH2:35][CH:36]([CH3:38])[CH3:37])=[N:23]\[C:24](=[O:33])[C:25]3[CH:30]=[CH:29][C:28]([F:31])=[C:27]([F:32])[CH:26]=3)[NH:18][N:17]=2)=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:32][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][C:28]=1[F:31])[C:24](/[N:23]=[C:22](\[NH:21][C:19]1[NH:18][N:17]=[C:16]([C:13]2[CH:14]=[CH:15][C:10]([CH2:9][OH:8])=[CH:11][CH:12]=2)[CH:20]=1)/[NH:34][CH2:35][CH:36]([CH3:38])[CH3:37])=[O:33]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178449204HCID 178449204, compound

Product 1

HCID 178449203HCID 178449203, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (Z)—N-(((3-(4-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)-1H-pyrazol-5-yl)amino)(isobutylamino)methylene)-3,4-difluorobenzamide (60 mg) in THF (2 mL) was added tetrabutylammonium fluoride (TBAF) (1 M in THF, 0.122 mL, 1.1 equiv). The solution was stirred at room temperature for one hour, and partitioned between water and EtOAc. The organic phase was dried over sodium sulfate, concentrated onto silica gel, and purified by silica chromatography to provide the title compound (23 mg, 49% yield). 1HNMR (400 MHz, DMSO-d6) δ 13.18 (s, 1H), 12.60 (s, 1H), 8.96 (t, 1H), 8.00 (m, 2H), 7.70 (d, 2H), 7.48 (m, 1H), 7.40 (d, 2H), 6.60 (s, 1H), 5.23 (t, 1H), 4.50 (d, 2H), 3.43 (m, 2H), 1.92 (m, 1H), 1.00 (d, 6H); MS (EI+) m/z: 428.07; HPLC (Method B): 4.67 min.

Workup

  1. custompartitioned between water and EtOAc
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated onto silica gel
  4. custompurified by silica chromatography

Sources & evidence

ORD record
ord-337ce0a31a98456aafe9c5eaa0c09d26
Source dataset
uspto-grants-2015_09
Patent number
US09139532B2

Reaction notes

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