Water → HCID 178426868, compound

HRID 2174010Notes

Reaction equation

HRID 2174010 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:13](=[O:14])[O:12][C:11]([C:19]3[NH:23][C:22]4[CH:24]=[CH:25][C:26]([C:28]#[N:29])=[CH:27][C:21]=4[N:20]=3)([C:15]([F:18])([F:17])[F:16])[C:5]2=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[Li+].[BH4-].O.[NH4+].[Cl-]>C1COCC1>[F:17][C:15]([F:16])([F:18])[C:11]([C:19]1[NH:23][C:22]2[CH:24]=[CH:25][C:26]([C:28]#[N:29])=[CH:27][C:21]=2[N:20]=1)([OH:12])[C:5]1[C:4]([CH2:13][OH:14])=[CH:3][C:2]([CH3:1])=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 178421813HCID 178421813, compound

Product 1

HCID 178426868HCID 178426868, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (±)-2-(5-methyl-3-oxo-1-(trifluoromethyl)-3,6-dihydro-1H-furo[3,4-e]indol-1-yl)-1H-benzo[d]imidazole-5-carbonitrile (47 mg, 0.119 mmol) in THF (0.5 mL) at 0° C., LiBH4 (2N in THF, 1.19 mL, 2.38 mmol) was added, followed by H2O (43 μL, 2.38 mmol). The reaction was stirred at 50° C. for 16 hours and then cooled to 0° C. A NH4Cl aqueous solution was added and the layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over Na2SO4. After concentration under reduced pressure, the residue was separated via silica gel flash column chromatography (CH2Cl2/EtOAc=0 to 100%) to give the title compound. 1H NMR (400 MHz, ACETONITRILE-d3 with about 3% METHANOL-d4) δ ppm 8.05 (s, 1H), 7.54-7.70 (m, 2H), 7.13 (s, 1H), 6.97 (d, J=3.2 Hz, 1H), 5.54 (br. s., 1H), 5.20 (d, J=12.8 Hz, 1H), 4.68 (d, J=12.0 Hz, 1H), 2.48 (s, 3H). HRMS calcd. for C20H16F3N4O2 (M+H)+ 401.122. found 401.1214.

Workup

  1. temperaturecooled to 0° C
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationAfter concentration under reduced pressure
  6. customthe residue was separated via silica gel flash column chromatography (CH2Cl2/EtOAc=0 to 100%)

Sources & evidence

ORD record
ord-c766231531814286b935973527a8d755
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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