Dimethylamine → HCID 18184491, compound

HRID 1358481Notes

Reaction equation

HRID 1358481 reaction equation
C[CH2:2][N:3](C(C)C)[CH:4](C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C1C2C(COC([N:54]3[CH2:62][C:61]4[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=4)[CH:55]3[C:63]([OH:65])=O)=O)C3C(=CC=CC=3)C=2C=CC=1.CNC>C(Cl)Cl.CCO>[CH3:2][N:3]([CH3:4])[C:63]([CH:55]1[C:56]2[C:61](=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH2:62][NH:54]1)=[O:65]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27561302-(9H-fluoren-9-ylmethoxycarbonyl)-1,3-dihydroisoindole-1-carboxylic Acid

Product 1

HCID 18184491HCID 18184491, compoundYield 204.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

1.66 g of DIPEA and then 5.73 g of BOP are added to a solution of 5 g of 2-(9-fluorenylmethoxycarbonyl)isoindoline-1-carboxylic acid (commercial) in 100 ml of DCM and the mixture is left stirring for 15 minutes at AT. 4.6 ml of a 5.6M solution of dimethylamine in EtOH are subsequently added and the mixture is left stirring for 30 minutes at AT. The reaction mixture is concentrated under vacuum, the residue is taken up in water and extracted with DCM, the organic phase is washed with a 5% KHSO4 solution and dried over Na2SO4, and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, elution being carried out with a DCM/AcOEt (70/30, v/v) mixture. 5 g of the expected product are obtained.

Workup

  1. waitthe mixture is left
  2. waitthe mixture is left
  3. stirringstirring for 30 minutes at AT
  4. concentrationThe reaction mixture is concentrated under vacuum
  5. extractionextracted with DCM
  6. washthe organic phase is washed with a 5% KHSO4 solution
  7. dry with materialdried over Na2SO4
  8. customthe solvent is evaporated under vacuum
  9. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-0efb4b204ee040a6b103e98a402b8f07
Source dataset
uspto-grants-2003_07
Patent number
US06596732B2

Reaction notes

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