Water → HCID 68181596, compound

HRID 1398706Notes

Reaction equation

HRID 1398706 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1([C:13]#[C:14][C:15]2[CH:16]=[CH:17][C:18]3[N:22]=[C:21]([CH3:23])[N:20]([C:24]4[N:29]=[CH:28][N:27]=[C:26]([NH2:30])[N:25]=4)[C:19]=3[CH:31]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[NH2:30][C:26]1[N:27]=[CH:28][N:29]=[C:24]([N:20]2[C:19]3[CH:31]=[C:15]([C:14]#[C:13][C:8]4([CH2:7][OH:6])[CH2:9][CH2:10][CH2:11][CH2:12]4)[CH:16]=[CH:17][C:18]=3[N:22]=[C:21]2[CH3:23])[N:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 137329571HCID 137329571, compound

Product 1

HCID 68181596HCID 68181596, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-{6-[1-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopentylethynyl]-2-methyl-benzoimidazol-1-yl}-[1,3,5]triazin-2-ylamine (6-e) (80 mg, 0.17 mmol) was dissolved in THF (100 mL), TBAF (113 mg, 0.43 mmol) was added. The resulting mixture was stirred at room temperature for 12 h. Water (5 mL) was added, extracted with EtOAc. The organic phase was concentrated, purified via prep-TLC separation to afford the title target (27.5 mg, 47%): 1H NMR (400 MHz, DMSO) delta 1.55-1.76 (m, 8H), 2.86 (s, 3H), 3.40 (d, J=4.8 Hz, 2H), 4.96 (t, J=4.8 Hz, 1H), 7.25 (d, J=8.4 Hz, 1H), 7.50 (d, J=8.4 Hz, 1H), 7.90-8.10 (m, 2H), 8.30 (t, J=0.8 Hz, 1H), 8.63 (s, 1H). LCMS: m/z=+349.1 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. concentrationThe organic phase was concentrated
  3. custompurified via prep-TLC separation
  4. customto afford the title target (27.5 mg, 47%)

Sources & evidence

ORD record
ord-afed54dc80f04f09a2b83db66614e942
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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