1,2-Dichloroethane → HCID 67494571, compound

HRID 241415Notes

Reaction equation

HRID 241415 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:16]1[NH:20][C:19]2[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:18]=2[N:17]=1.[CH3:27][O:28][CH2:29][CH2:30][NH2:31].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>CN(C=O)C.O>[CH3:27][O:28][CH2:29][CH2:30][NH:31][C:13]([C:11]1[S:12][C:8]([C:5]2[CH:6]=[N:7][C:2]([NH2:1])=[C:3]([C:16]3[NH:20][C:19]4[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:18]=4[N:17]=3)[CH:4]=2)=[CH:9][CH:10]=1)=[O:15]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 80182-MethoxyethylamineHCID 757711-HydroxybenzotriazoleHCID 66886573HCID 66886573, compound

Product 1

HCID 67494571HCID 67494571, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

14.2 157 mg (0.111 mmol) of 5-[6-amino-5-(6-methoxy-1H-benzimidazol-2-yl)pyridin-3-yl]thiophene-2-carboxylic acid are dissolved in 0.5 ml of DMF. 10 μl (0.114 mmol) of 2-methoxyethylamine, 14.9 mg (0.111 mmol) of HOBt, 21.2 mg (0.111 mmol) of EDC and 24.3 μl (0.221 mmol) of N-methylmorpholine are added. The reaction mixture is stirred at room temperature for 14 h, water is added, and the mixture is extracted with ethyl acetate. The organic phases are dried using sodium sulfate, filtered and evaporated. The residue is purified by means of RP-HPLC and lyophilised, giving N-(2-methoxyethyl)-5-[6-amino-5-(6-methoxy-1H-benzimidazol-2-yl)pyridin-3-yl]-thiophene-2-carboxamide; HPLC-MS [M+H]+ 424.2.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. customThe organic phases are dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified by means of RP-HPLC

Sources & evidence

ORD record
ord-e2e4f767abf24e978010e63637652f4f
Source dataset
uspto-grants-2014_02
Patent number
US08648201B2

Reaction notes

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