Diisopropylethylamine → HCID 178462095, compound

HRID 551168Notes

Reaction equation

HRID 551168 reaction equation
[N:1]1([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][C:2]1=[O:7].CCN(C(C)C)C(C)C.Cl.[Cl:27][C:28]1[CH:39]=[CH:38][C:31]2[NH:32][C:33]([C@@H:35]([NH2:37])[CH3:36])=[N:34][C:30]=2[CH:29]=1>CN(C=O)C>[Cl:27][C:28]1[CH:39]=[CH:38][C:31]2[NH:32][C:33]([C@@H:35]([NH:37][C:12](=[O:14])[C:11]3[CH:10]=[CH:9][C:8]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][C:2]4=[O:7])=[CH:16][CH:15]=3)[CH3:36])=[N:34][C:30]=2[CH:29]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 230877894-(3-Oxomorpholino)benzoic acidHCID 178461860(1S)-1-(5-chloro-1h-benzimidazol-2-yl)-ethylamine-hydrochloride

Product 1

HCID 178462095HCID 178462095, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

254 mg (1.15 mmol) 4-(morpholin-3-on-4-yl)-benzoic acid (prepared by synthesis sequence analogously to Example 30a, 2d and 21a) are placed in 5 ml DMF and 428 mg (1.0 mmol) PfTU and 514 μl (3.0 mmol) DIPEA are added. After stirring at ambient temperature for 10 minutes 232 mg (1.0 mmol) (1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamine-hydrochloride are added and the mixture is stirred for 16 hours at ambient temperature. Then the reaction mixture is filtered through basic aluminium oxide and evaporated down i. vac. The residue is purified by chromatography on silica gel (eluting gradient: dichloromethane/methanol 100:0->90:10), the corresponding fractions are evaporated down i. vac., the residue is dissolved in acetonitrile/water and lyophilised.

Workup

  1. additionare added
  2. filtrationThen the reaction mixture is filtered through basic aluminium oxide
  3. customevaporated down i
  4. customThe residue is purified by chromatography on silica gel (eluting gradient: dichloromethane/methanol 100:0->90:10)
  5. customthe corresponding fractions are evaporated down i
  6. dissolution, the residue is dissolved in acetonitrile/water

Sources & evidence

ORD record
ord-c051a33371ab4861b1464e5a4321bbd1
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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