Hydrochloric Acid → 1-(1-ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid (1-pyridin-2-yl-butyl)-amide

HRID 1750176Notes

Reaction equation

HRID 1750176 reaction equation
[CH2:1]([CH:3]([N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]([OH:17])=O)=[CH:14][C:9]=2[N:8]=[C:7]1[CH2:18][C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[CH2:4][CH3:5])[CH3:2].C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[N:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[CH:49]([NH2:53])[CH2:50][CH2:51][CH3:52].Cl>CN(C=O)C.O.C(Cl)CCl>[N:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[CH:49]([NH:53][C:15]([C:13]1[CH:12]=[CH:11][C:10]2[N:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[C:7]([CH2:18][C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)=[N:8][C:9]=2[CH:14]=1)=[O:17])[CH2:50][CH2:51][CH3:52]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 227675931-(Pyridin-2-yl)butan-1-amineHCID 867143731-(1-ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid

Product 1

HCID 867143891-(1-ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid (1-pyridin-2-yl-butyl)-amideYield 100%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 50 mg of 1-(1-ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid in 2 ml of dry DMF 10 mg of HOAT, 35 mg of EDC and 0.1 ml of DIPEA were added at 0° C. After 15 min 25 mg of 1-pyridin-2-ylbutylamine were added and the reaction was stirred at rt for 16 h. The reaction was then poured into water and the pH was adjusted to 4 by the addition of 2 M aqueous hydrochloric acid. The reaction was extracted with ethyl acetate three times. The combined organic phases were dried over magnesium sulphate and concentrated. 70 mg (100%) of 1-(1-ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid (1-pyridin-2-yl-butyl)-amide were obtained.

Workup

  1. extractionThe reaction was extracted with ethyl acetate three times
  2. dry with materialThe combined organic phases were dried over magnesium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-51d50f83f51a486189e2f342e8a54619
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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