1,2-Dichloroethane → HCID 178522830, compound

HRID 1596526Notes

Reaction equation

HRID 1596526 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 (0.007 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) δ 7.40-7.20 (m, 9H), 4.39 (s, 2H), 3.55 (m, 1H), 2.31 (m, 1H), 2.20 (br d, 2H), 1.98 (br d, 2H), 1.77 (m, 2H), 1.50 (m, 2H); 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-693d261f64c947a7b4b8feb0d5045fbe
Source dataset
uspto-grants-2001_09
Patent number
US06291499B1

Reaction notes

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