1,2-Dichloroethane → HCID 178522830, compound

HRID 2298972Notes

Reaction equation

HRID 2298972 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]([OH:19])=O)[CH2:13][CH2:12]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[CH2:41]([NH2:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>CN(C=O)C>[CH2:41]([NH:48][C:17]([C@H:14]1[CH2:13][CH2:12][C@H:11]([NH:10][C:2]2[NH:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=2)[CH2:16][CH2:15]1)=[O:19])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 7504BenzylamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 178525758HCID 178525758, compound

Product 1

HCID 178522830HCID 178522830, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of trans 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid (M) (20 mg, 0.07 mmol) in DMF (0.2 mL) was added EDC (26 mg, 0.14 mmol), HOBt (18 mg, 0.14 mmol), triethylamine (0.019 mL, 0.14 mmol) and benzyl amine (0.007 mL, 0.7 mmol). The reaction mixture was stirred at room temperature for 1 h followed by quenching with aqueous NaHCO3 and EtOAc. The layers were separated and the organic was washed twice with water, dried over Na2SO4, filtered and concentrated. Purification of the crude oil by preparative reverse-phase HPLC gave trans 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid benzylamide (Example 9) (14 mg): 1H NMR (300 MHz, CD3OD) δ7.40-7.20 (m, 9 H), 4.39 (s, 2 H), 3.55 (m, 1 H), 2.31 (m, 1 H), 2.20 (br d, 2 H), 1.98 (br d, 2 H), 1.77 (m, 2 H), 1.50 (m, 2 H); mass spectrum m/z 349 [(M+H)+; calcd for C21H25N4O: 349].

Workup

  1. customby quenching with aqueous NaHCO3 and EtOAc
  2. customThe layers were separated
  3. washthe organic was washed twice with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the crude oil by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-5efdb9be8c164755b1f1a49aec69a0b5
Source dataset
uspto-grants-2002_12
Patent number
US06495561B2

Reaction notes

Loading…