Diisopropylethylamine → HCID 67089308, compound

HRID 2075400Notes

Reaction equation

HRID 2075400 reaction equation
C1C2C(=CC(C3SC(NC[CH:18]([OH:21])CC)=NN=3)=CC=2)C=CN=1.CN(C(ON1N=N[C:32]2[CH:33]=[CH:34][CH:35]=N[C:31]1=2)=[N+](C)C)C.[F:39][P-](F)(F)(F)(F)F.CC[N:48]([CH:52]([CH3:54])C)[CH:49]([CH3:51])C.[C:55]([O:59][C:60]([NH:62][C@@H:63]([CH2:70][C:71]1[CH:72]=[N:73][C:74]([C:77]([F:80])([F:79])[F:78])=[CH:75][CH:76]=1)[CH2:64][CH2:65][C:66]([NH:68][NH2:69])=[O:67])=[O:61])([CH3:58])([CH3:57])[CH3:56]>CN(C=O)C>[C:55]([O:59][C:60]([NH:62][C@@H:63]([CH2:70][C:71]1[CH:72]=[N:73][C:74]([C:77]([F:80])([F:78])[F:79])=[CH:75][CH:76]=1)[CH2:64][CH2:65][C:66]([NH:68][NH:69][C:18]([C:33]1[CH:34]=[C:35]2[C:51](=[CH:31][CH:32]=1)[CH:49]=[N:48][C:52]([F:39])=[CH:54]2)=[O:21])=[O:67])=[O:61])([CH3:58])([CH3:56])[CH3:57]

Participants

6

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57991899HCID 57991899, compoundHCID 57991958HCID 57991958, compound

Product 1

HCID 67089308HCID 67089308, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 3-fluoroisoquinoline-6-carboxylic acid (123 mg, 644 μmol)(prepared as shown in Scheme 23), HATU (245 mg, 644 μmol), and DIEA (122 μl, 698 μmol) in DMF (5 mL) was stirred at room temperature for 15 minutes. This mixture was added dropwise to a mixture of (R)-4-(tert-butoxycarbonylamino)-5-(6-(trifluoromethyl)pyridin-3-yl)pentanehydrazide (202 mg, 537 μmol) and DIEA (122 μL, 698 μmol) in DMF (5 mL), and the resulting mixture was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure and the residue was partitioned between saturated aqueous NaHCO3 (20 mL) and DCM (20 mL). The layers were separated and the aqueous layer was extracted with DCM (2×20 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The resulting white solid was recrystallized from EtOAc to deliver (R)—N′-(4-(tert-butoxycarbonylamino)-5-(6-(trifluoromethyl)pyridin-3-yl)pentanoyl)-3-fluoroisoquinoline-6-carbohydrazide (218 mg, 74%) as a white solid. LCMS (API-ES) m/z: 572.0 (M+Na+).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between saturated aqueous NaHCO3 (20 mL) and DCM (20 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with DCM (2×20 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting white solid was recrystallized from EtOAc

Sources & evidence

ORD record
ord-d8b0d1e47c7c4f8a96d2fe386a7a6776
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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