Triethylamine → HCID 131727597, compound

HRID 2106522Notes

Reaction equation

HRID 2106522 reaction equation
CN(C([O:8]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N([CH2:28][CH3:29])CC)C.[OH:30][CH2:31][C:32]([N:34]([CH3:36])[CH3:35])=[O:33].[O:37]=[C:38]1[N:44]([CH:45]2[CH2:50][CH2:49][N:48]([C:51]([O:53][C@H:54]([CH2:73][C:74]3[CH:79]=[C:78]([C:80]([F:83])([F:82])[F:81])[C:77]([NH2:84])=[C:76]([Cl:85])[CH:75]=3)[C:55]([N:57]3[CH2:62][CH2:61][CH:60]([CH:63]4[CH2:68][CH2:67][N:66](CC(O)=O)[CH2:65][CH2:64]4)[CH2:59][CH2:58]3)=[O:56])=[O:52])[CH2:47][CH2:46]2)[CH2:43][CH2:42][C:41]2[CH:86]=[CH:87][CH:88]=[CH:89][C:40]=2[NH:39]1>CN(C=O)C>[O:37]=[C:38]1[N:44]([CH:45]2[CH2:50][CH2:49][N:48]([C:51]([O:53][C@H:54]([CH2:73][C:74]3[CH:79]=[C:78]([C:80]([F:81])([F:83])[F:82])[C:77]([NH2:84])=[C:76]([Cl:85])[CH:75]=3)[C:55]([N:57]3[CH2:58][CH2:59][CH:60]([CH:63]4[CH2:68][CH2:67][N:66]([O:30][CH2:31][C:32](=[O:33])[N:34]([CH3:36])[CH3:35])[CH2:65][CH2:64]4)[CH2:61][CH:62]3[CH:29]=[C:28]=[O:8])=[O:56])=[O:52])[CH2:47][CH2:46]2)[CH2:43][CH2:42][C:41]2[CH:86]=[CH:87][CH:88]=[CH:89][C:40]=2[NH:39]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 128746822-Hydroxy-N,N-dimethylacetamideHCID 16045802HCID 16045802, compound

Product 1

HCID 131727597HCID 131727597, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

48 mg (0.15 mmol) TBTU, 21 μL (0.15 mmol) triethylamine and 15 mg (0.15 mmol) 2-hydroxy-N,N-dimethyl-acetamide were added to a solution of 100 mg (0.13 mmol) (R)-1-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-(1′-carboxymethyl-4,4′-bipiperidinyl-1-yl)-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate in 1 mL DMF and the reaction mixture was stirred overnight at RT. The reaction solution was filtered through a syringe filter and the crude product was purified by HPLC. The fractions containing the product were combined and evaporated down i. vac.

Workup

  1. filtrationThe reaction solution was filtered through a syringe
  2. filtrationfilter
  3. customthe crude product was purified by HPLC
  4. additionThe fractions containing the product
  5. customevaporated down i

Sources & evidence

ORD record
ord-a1a63415fb7d4ca3b974aaec19c42694
Source dataset
uspto-grants-2009_08
Patent number
US07579341B2

Reaction notes

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