Tetrahydrofuran → HCID 178424042, compound

HRID 2174018Notes

Reaction equation

HRID 2174018 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([C:11]([C:13]3[NH:17][C:16]4[CH:18]=[CH:19][C:20]([C:22]#[N:23])=[CH:21][C:15]=4[N:14]=3)=[O:12])=[C:8]([CH3:24])[CH:7]=[C:6]([CH3:25])[C:5]=2[NH:4][CH:3]=1.[Li+].[BH4-].C1COCC1>>[OH:12][CH:11]([C:9]1[C:8]([CH3:24])=[CH:7][C:6]([CH3:25])=[C:5]2[C:10]=1[C:2]([CH3:1])=[CH:3][NH:4]2)[C:13]1[NH:17][C:16]2[CH:18]=[CH:19][C:20]([C:22]#[N:23])=[CH:21][C:15]=2[N:14]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 178424041HCID 178424041, compound

Product 1

HCID 178424042HCID 178424042, compound

Procedure

A solution of 2-(3,5,7-trimethyl-1H-indole-4-carbonyl)-1H-benzo[d]imidazole-5-carbonitrile (20 mg, 0.061 mmol) and LiBH4 in THF (2M, 2 mL, 4.00 mmol) was stirred at 50° C. for 2 h. The reaction mixture was cooled to room temperature. The mixture was quenched by half satd. aq. KHSO4 and basified by 5% NaHCO3. The layers were separated and the aqueous layer was extracted with CH2Cl2/2,2,2-trifluoroethanol (c.a. 9/1). The organic phase was washed with H2O and brine, dried over Na2SO4, and filtered. After concentration of the filtrate the resulting residue was purified by RP-HPLC (HC-A) to give the title compound. 1H NMR (400 MHz, ACETONITRILE-d3 with about 5 μL TFA) δ ppm 9.10 (br. s., 1H), 8.08 (s, 1H), 7.73-7.82 (m, 2H), 7.06 (s, 1H), 6.96 (s, 1H), 6.84 (s, 1H), 2.45 (s, 3H), 2.21 (br. s., 3H), 2.19 (s, 3H). HRMS calcd. for C20H18N4O (M+H)+ 331.1554. found 331.1555.

Workup

  1. customThe mixture was quenched by half satd
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2/2,2,2-trifluoroethanol (c.a. 9/1)
  4. washThe organic phase was washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customAfter concentration of the filtrate the resulting residue was purified by RP-HPLC (HC-A)

Sources & evidence

ORD record
ord-4404e239a9cc4e7dbd335543e2302047
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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