3,4-Diaminopyridine → HCID 20680750, compound

HRID 651665Notes

Reaction equation

HRID 651665 reaction equation
C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH3:16][O:17][C:18]1[CH:27]=[C:26]2[C:21]([CH:22]=[CH:23][C:24]([S:28]([NH:31][C@H:32]3[CH2:36][CH2:35][N:34]([CH2:37][C:38](O)=[O:39])[C:33]3=[O:41])(=[O:30])=[O:29])=[CH:25]2)=[CH:20][CH:19]=1.[NH2:42][C:43]1[CH:44]=[N:45][CH:46]=[CH:47][C:48]=1[NH2:49]>C1COCC1.CN(C=O)C>[NH2:42][C:43]1[CH:44]=[N:45][CH:46]=[CH:47][C:48]=1[NH:49][C:38](=[O:39])[CH2:37][N:34]1[CH2:35][CH2:36][C@H:32]([NH:31][S:28]([C:24]2[CH:23]=[CH:22][C:21]3[C:26](=[CH:27][C:18]([O:17][CH3:16])=[CH:19][CH:20]=3)[CH:25]=2)(=[O:29])=[O:30])[C:33]1=[O:41]

Participants

7

Reactant 4

HCID 59183,4-DiaminopyridineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 20680701HCID 20680701, compound

Product 1

HCID 20680750HCID 20680750, compoundYield 44.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.13 g, 1.3 mmol) and isobutyl chloroformate (0.18 g, 1.3 mmol) are added to a solution of [3-(S)-(7-methoxy-naphthalene-2-sulfonylamino)-2-oxopyrrolidin-1-yl]-acetic acid (0.5 g, 1.3 mmol) in THF (15 mL) at −10° C. The mixture is stirred for 20 minutes then treated with a solution of 3,4-diaminopyridine (0.16 g, 1.5 mmol) in DMF (5 mL). The resulting mixture is warmed to room temperature and stirred for 3 hours. The reaction mixture is concentrated in vacuo, then diluted with methylene chloride. The organic layer is washed with brine, dried over MgSO4, filtered and concentrated. The residue is purified by flash chromatography (5-8% MeOH/CH2Cl2). to give the title compound (0.27 g, 0.58 mmol) as a solid.

Workup

  1. stirringstirred for 3 hours
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. additiondiluted with methylene chloride
  4. washThe organic layer is washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified by flash chromatography (5-8% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-4e9fcb7fab8c4b12af1797b7bb604665
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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