Triethylamine → HCID 68680560, compound

HRID 2265895Notes

Reaction equation

HRID 2265895 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Br:34][C:35]1[CH:36]=[CH:37][C:38]([OH:67])=[C:39]2[C:44]=1[CH:43]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[N:42]([S:50]([C:53]1[CH:58]=[CH:57][C:56]([O:59][C:60]3[CH:65]=[CH:64][C:63]([F:66])=[CH:62][CH:61]=3)=[CH:55][CH:54]=1)(=[O:52])=[O:51])[CH2:41][CH2:40]2.C(N(CC)CC)C.[N:75]1([CH2:81][CH2:82]O)[CH2:80][CH2:79][CH2:78][CH2:77][CH2:76]1>ClCCl>[Br:34][C:35]1[CH:36]=[CH:37][C:38]([O:67][CH2:82][CH2:81][N:75]2[CH2:80][CH2:79][CH2:78][CH2:77][CH2:76]2)=[C:39]2[C:44]=1[CH:43]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[N:42]([S:50]([C:53]1[CH:58]=[CH:57][C:56]([O:59][C:60]3[CH:61]=[CH:62][C:63]([F:66])=[CH:64][CH:65]=3)=[CH:55][CH:54]=1)(=[O:52])=[O:51])[CH2:41][CH2:40]2

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 18232N-PiperidinoethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 68681861HCID 68681861, compound

Product 1

HCID 68680560HCID 68680560, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.515 g of PPh3 (polymer-bound, 1.2-1.5 mmol/g) are mixed with 0.13 g of diisopropyl azodicarboxylate in 5 ml of dichloromethane and shaken at room temperature for 15 min. Then 0.17 g (0.31 mmol) of ethyl 8-bromo-2-[4-(4-fluorophenoxy)benzene-sulfonyl]-5-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate (crude product, 21D), 0.031 g (0.31 mmol) of triethylamine and 0.04 g (0.31 mmol) of 2-piperidin-1-ylethanol are added, and the mixture is shaken at room temperature until no further increase in conversion can be detected by means of an LCMS check. For workup, the mixture is filtered and the filtrate is washed twice with H2O. The aqueous phases are extracted twice with dichloromethane. The combined organic phases dried with MgSO4 and evaporated. The crude product obtained in this way is purified by prep. HPLC, resulting in 0.08 g of the title compound as trifluoroacetate.

Workup

  1. stirringthe mixture is shaken at room temperature until
  2. temperatureno further increase in conversion
  3. filtrationFor workup, the mixture is filtered
  4. washthe filtrate is washed twice with H2O
  5. extractionThe aqueous phases are extracted twice with dichloromethane
  6. dry with materialThe combined organic phases dried with MgSO4
  7. customevaporated
  8. customThe crude product obtained in this way
  9. customis purified by prep

Sources & evidence

ORD record
ord-ba5fc98992294722811ef84ecbd0032c
Source dataset
uspto-grants-2010_12
Patent number
US07858619B2

Reaction notes

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