Diisopropylethylamine → HCID 67681934, compound

HRID 1751358Notes

Reaction equation

HRID 1751358 reaction equation
[F:1][CH:2]([F:15])[O:3][C@H:4]([CH3:14])[C@H:5]([NH:9][C:10]([O:12][CH3:13])=[O:11])[C:6]([OH:8])=O.[NH:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]1[NH:22][C:23]([C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[C:31]([B:36]4[O:40][C:39]([CH3:42])([CH3:41])[C:38]([CH3:44])([CH3:43])[O:37]4)[CH:32]=3)[CH:27]=2)=[CH:24][N:25]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[F:15][CH:2]([F:1])[O:3][C@H:4]([CH3:14])[C@H:5]([NH:9][C:10](=[O:11])[O:12][CH3:13])[C:6](=[O:8])[N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]1[NH:22][C:23]([C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[C:31]([B:36]4[O:40][C:39]([CH3:42])([CH3:41])[C:38]([CH3:44])([CH3:43])[O:37]4)[CH:32]=3)[CH:27]=2)=[CH:24][N:25]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69675543HCID 69675543, compoundHCID 86702706HCID 86702706, compound

Product 1

HCID 67681934HCID 67681934, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,3R)-3-(difluoromethoxy)-2-(methoxycarbonylamino)butanoic acid (205 mg, 0.9 mmol) and (S)-2-(pyrrolidin-2-yl)-5-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)-1H-imidazole (315 mg, 0.8 mmol) in dimethylformamide (8 mL) was added HATU (325 mg, 0.85 mmol) and diisopropylethylamine (0.565 mL, 3.2 mmol). The reaction was stirred for 1 hour and then diluted with ethyl acetate. The organic layer was washed twice with saturated NaHCO3 solution and brine, dried (MgSO4) and concentrated. The resulting residue was purified by flash chromatography to yield methyl (2S,3R)-3-(difluoromethoxy)-1-oxo-1-((S)-2-(5-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)butan-2-ylcarbamate (230 mg, 47%). LCMS-ESI+: calculated for C30H37BF2N4O6: 598.45; observed [M+1]+: 599.31.

Workup

  1. washThe organic layer was washed twice with saturated NaHCO3 solution and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e87066876c734d49b8361ae140f6bbad
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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