Dimethylamine → HCID 57780542, compound

HRID 1095380Notes

Reaction equation

HRID 1095380 reaction equation
Cl.[N:2]1([CH2:8][CH2:9][N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]([C:19]([NH:21][C@H:22]([C:27](O)=[O:28])[C@H:23]([CH2:25][CH3:26])[CH3:24])=[O:20])[C:11]2=[O:30])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.C1N=[CH:34][N:33](C(N2C=NC=C2)=O)[CH:32]=1.CNC.O>CN(C=O)C>[CH3:32][N:33]([CH3:34])[C:27]([C@@H:22]([NH:21][C:19]([N:12]1[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:10]([CH2:9][CH2:8][N:2]2[CH2:3][CH2:4][O:5][CH2:6][CH2:7]2)[C:11]1=[O:30])=[O:20])[C@@H:23]([CH3:24])[CH2:25][CH3:26])=[O:28]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 60209093HCID 60209093, compound

Product 1

HCID 57780542HCID 57780542, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-{[3-(2-morpholin-4-ylethyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]carbonyl}-L-isoleucine hydrochloride (Step 1, 62 mg, 0.14 mmol) in DMF (1 mL) was added CDI (27 mg, 0.17 mol) at rt. After 2 h, to the mixture was added aq. dimethylamine (40%, 20 μL) and stirred for further 14 h. Then to the mixture was added water (10 mL). The mixture was extracted with ethyl acetate (20 mL×2) and the combined organic layers were washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by preparative TLC eluting with dichloromethane/methanol (10/1) to afford 33 mg (54%) of the title compound.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (20 mL×2)
  2. washthe combined organic layers were washed with brine (10 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC
  7. washeluting with dichloromethane/methanol (10/1)

Sources & evidence

ORD record
ord-c075a127a6714a389452d8012393a5eb
Source dataset
uspto-grants-2012_03
Patent number
US08138177B2

Reaction notes

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