1-Pyrrolidinecarbonyl chloride → HCID 21479140, compound

HRID 2292726Notes

Reaction equation

HRID 2292726 reaction equation
[N:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:9][C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[C:16]([CH2:18][CH2:19][CH2:20][CH3:21])[N:15]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]4[C:30]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[CH:31][CH:32]=[CH:33][CH:34]=4)=[CH:25][CH:24]=3)[C:14]=2[CH:42]=1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[CH2:18]([C:16]1[N:15]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]3[C:30]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[CH:31][CH:32]=[CH:33][CH:34]=3)=[CH:27][CH:28]=2)[C:14]2[CH:42]=[C:10]([NH:9][C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:7])[CH:11]=[CH:12][C:13]=2[N:17]=1)[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 2

HCID 709371-Pyrrolidinecarbonyl chlorideHCID 10389303HCID 10389303, compound

Product 1

HCID 21479140HCID 21479140, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

2.0 g (15 mMol) of pyrrolidinocarbonyl chloride are placed in 50 ml of dry chloroform and 2.3 g (6 mMol) of tert.-butyl 4'-[(6-amino-2-n-butyl-benzimidazol-1-yl)-methyl]biphenyl-2-carboxylate dissolved in 50 ml of dry pyridine are added dropwise for one hour. The reaction solution is stirred for a further 24 hours and then concentrated by rotary evaporation. The oily residue is distributed in ethyl acetate and 10% sodium hydrogen carbonate solution, the organic phase is separated off and, after drying with magnesium sulphate, concentrated by rotary evaporation. Purification is carried out using a silica gel column (particle size: 0.063-0.2 mm), eluting with petroleum ether/ethyl acetate=3:7. The corresponding column fractions are concentrated by rotary evaporation and dried in vacuo at 50° C.

Workup

  1. additionare added dropwise for one hour
  2. concentrationconcentrated by rotary evaporation
  3. custom10% sodium hydrogen carbonate solution, the organic phase is separated off
  4. dry with materialafter drying with magnesium sulphate
  5. concentrationconcentrated by rotary evaporation
  6. customPurification
  7. washeluting with petroleum ether/ethyl acetate=3:7
  8. concentrationThe corresponding column fractions are concentrated by rotary evaporation
  9. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-fe650139e6bf4cbe9d09bc76eba121ba
Source dataset
uspto-grants-1997_11
Patent number
US05684029

Reaction notes

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