Triethylamine → HCID 66942052, compound

HRID 2267238Notes

Reaction equation

HRID 2267238 reaction equation
CN([C:4]([O:8]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:23](N(CC)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]([N: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[CH2:46][CH2:47][N:48]([C:51]([O:53][C@H:54]([CH2:73][C:74]3[CH:79]=[C:78]([C:80]([F:82])([F:81])[F:83])[C:77]([NH2:84])=[C:76]([Cl:85])[CH:75]=3)[C:55]([N:57]3[CH2:58][CH2:59][CH:60]([N:63]4[CH2:64][CH2:65][N:66]([C:4]([O:30][CH2:31][C:32](=[O:33])[N:34]([CH3:36])[CH3:35])=[O:8])[CH2:67][CH:68]4[CH3:23])[CH2:61][CH2:62]3)=[O:56])=[O:52])[CH2:49][CH2:50]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 57807453HCID 57807453, compound

Product 1

HCID 66942052HCID 66942052, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

90 mg (0.28 mmol) TBTU, 39 μL (0.15 mmol) triethylamine and 29 mg (0.28 mmol) 2-hydroxy-N,N-dimethyl-acetamide were added to a solution of 190 mg (0.25 mmol) (R)-1-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-[4-(4-carboxymethyl-piperazin-1-yl)-piperidin-1-yl]-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate in 5 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 freeze-dried.

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. customfreeze-dried

Sources & evidence

ORD record
ord-894ded508fb0426ebb5fa894c394f21a
Source dataset
uspto-grants-2010_12
Patent number
US07858622B2

Reaction notes

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