1,2-Dichloroethane → HCID 90414231, compound

HRID 1776735Notes

Reaction equation

HRID 1776735 reaction equation
[CH:1]([C:3]1[CH:37]=[CH:36][C:6]([CH2:7][N:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17][CH2:18][C:19]4[CH:28]=[CH:27][C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:20]=4)=[CH:16][C:11]=3[N:10]=[C:9]2[CH2:29][C:30]([CH3:35])([CH3:34])[C:31]([OH:33])=[O:32])=[CH:5][CH:4]=1)=[O:2].F[C:39]1(F)CCCN[CH2:40]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].ClCCCl>C(Cl)Cl.O>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17][CH2:18][C:19]4[CH:28]=[CH:27][C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:20]=4)=[CH:16][C:11]=3[N:10]=[C:9]2[CH2:29][C:30]([CH3:35])([CH3:34])[C:31]([O:33][CH2:39][CH3:40])=[O:32])=[CH:36][CH:37]=1)=[O:2]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 27583503,3-DifluoropiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 90416824HCID 90416824, compound

Product 1

HCID 90414231HCID 90414231, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a 10 mL flask were added 3-(1-(4-formylbenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoic acid (160 mg, 0.31 mmol), 3,3-difluoropiperidine (58 mg, 0.37 mmol), sodium triacetoxyborohydride (130 mg, 0.61 mmol) and DCE (3.0 mL) and was stirred at RT overnight. The mixture was diluted with DCM (5 mL) and poured into water (10 mL) then extracted with DCM (3×10 mL), dried over Na2SO4, and concentrated to dryness. The residue was purified using FCC to provide the title compound. MS (ESI): mass calcd. for C37H40F2N4O3, 626.75; m/z found, 627.2 [M+H]+. 1H NMR (600 MHz, CDCl3) δ 8.17 (d, J=8.5, 1H), 8.09 (d, J=8.5, 1H), 7.80 (t, J=11.1, 1H), 7.72 (ddd, J=13.3, 7.6, 3.9, 2H), 7.55-7.50 (m, 1H), 7.35 (d, J=2.3, 1H), 7.22 (t, J=10.3, 2H), 7.07 (t, J=10.5, 1H), 6.99-6.93 (m, 3H), 5.42 (s, 2H), 5.34 (s, 2H), 4.09 (q, J=7.1, 2H), 3.53 (s, 2H), 3.05 (s, 2H), 2.61-2.53 (m, 2H), 2.40 (dd, J=16.1, 11.1, 2H), 1.90-1.80 (m, 2H), 1.78-1.70 (m, 2H), 1.36 (s, 6H), 1.16 (t, J=7.1, 3H).

Workup

  1. extractionthen extracted with DCM (3×10 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to dryness
  4. customThe residue was purified

Sources & evidence

ORD record
ord-e44fe8482aca4a2fbc3b76debf0814df
Source dataset
uspto-grants-2016_02
Patent number
US09265770B2

Reaction notes

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