Diisopropylethylamine → HCID 68283908, compound

HRID 1527435Notes

Reaction equation

HRID 1527435 reaction equation
Cl.[CH2:2]([O:5][C:6]([C@@H:8]1[CH2:13][C@@H:12]2[C@@H:10]([CH2:11]2)[N:9]1[C:14]([OH:16])=O)=[O:7])[CH:3]=[CH2:4].[C:17]([C:20]1[C:28]2[C:23](=[N:24][CH:25]=[CH:26][CH:27]=2)[N:22]([CH2:29]C(O)=O)[N:21]=1)(=[O:19])[CH3:18].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:2]([O:5][C:6]([C@@H:8]1[CH2:13][C@@H:12]2[C@@H:10]([CH2:11]2)[N:9]1[C:14](=[O:16])[CH2:29][N:22]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:28]2[C:20]([C:17](=[O:19])[CH3:18])=[N:21]1)=[O:7])[CH:3]=[CH2:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68283436HCID 68283436, compoundHCID 68284020HCID 68284020, compound

Product 1

HCID 68283908HCID 68283908, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1R,3S,5R)-2-azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid 3-allyl ester hydrochloride (1.03 g, 6.43 mmol), (3-acetyl-pyrazolo[3,4-b]pyridin-1-yl)acetic acid (prepared as described in Part A, 1.3 g, 5.93 mmol) and HBTU (2.70 g, 7.12 mmol) in DMF (19.7 mL) was added DIPEA (3.11 mL, 17.8 mmol). The reaction mixture was stirred for 16 h at RT. DMF was evaporated. The residue was poured into NH4Cl (saturated aqueous solution) and extracted with EtOAc (3×50 mL). The organic phases were combined, dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 0:10). Rf, TLC (EtOAc)=0.6; MS (LCMS): 369.0 [M+H]+, 391.0 [MH+Na]+; tR (HPLC conditions k): 2.78 min.

Workup

  1. customDMF was evaporated
  2. additionThe residue was poured into NH4Cl (saturated aqueous solution)
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 0:10)
  8. custom2.78 min.

Sources & evidence

ORD record
ord-0112d6f93dd840a6a4af7fb329088bb6
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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