1,2-Dichloroethane → HCID 68670892, compound

HRID 2047408Notes

Reaction equation

HRID 2047408 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][C:3]=1[C:15]1[NH:19][C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[N:16]=1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[C:41]([O:45][C:46]([N:48]1[CH2:53][CH2:52][CH2:51][CH:50]([C:54](O)=[O:55])[CH2:49]1)=[O:47])([CH3:44])([CH3:43])[CH3:42].C(Cl)CCl>C(Cl)Cl.O>[C:41]([O:45][C:46]([N:48]1[CH2:53][CH2:52][CH2:51][CH:50]([C:54]([N:11]2[CH2:12][CH2:13][CH2:14][N:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:15]4[NH:16][C:17]5[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=5[N:19]=4)[CH:4]=3)[CH2:9][CH2:10]2)=[O:55])[CH2:49]1)=[O:47])([CH3:44])([CH3:43])[CH3:42]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acidHCID 68670057HCID 68670057, compound

Product 1

HCID 68670892HCID 68670892, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

2-(2-Chloro-5-[1,4]diazepan-1-yl-phenyl)-1H-benzoimidazole (0.25 g, 0.76 mmol), HOBt (0.12 g, 0.86 mmol), NMM (0.5 mL, 3.9 mmol), piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (0.17 g, 0.76 mmol), and EDC (0.22 g, 1.16 mmol) were dissolved in DCM (8.0 mL) and stirred at 20° C. for 16 h. Water (6.0 mL) was added. Organic layer was separated, concentrated under reduced pressure and crude was purified by flash chromatography (eluent: 100% of AcOEt) to afford 0.25 g of the title compound. (100%).

Workup

  1. customOrganic layer was separated
  2. concentrationconcentrated under reduced pressure and crude
  3. customwas purified by flash chromatography (eluent: 100% of AcOEt)

Sources & evidence

ORD record
ord-881730d04ea447f69e411434918be59c
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Reaction notes

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