Diisopropylethylamine → HCID 67966820, compound

HRID 527529Notes

Reaction equation

HRID 527529 reaction equation
[CH2:1]([C:3]1[C:7]2[C:8]([O:12][C:13]3[N:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=3)=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][N:4]=1)[CH3:2].[CH3:20][C:21]([O:24][C:25]([NH:27][C@H:28]([CH2:32][CH3:33])[C:29](O)=[O:30])=[O:26])([CH3:23])[CH3:22].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:1]([C:3]1[C:7]2[C:8]([O:12][C:13]3[N:18]=[CH:17][C:16]([NH:19][C:29]([C@H:28]([NH:27][C:25](=[O:26])[O:24][C:21]([CH3:23])([CH3:22])[CH3:20])[CH2:32][CH3:33])=[O:30])=[CH:15][CH:14]=3)=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2755936(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 679605196-[(3-Ethyl-1,2-benzisoxazol-4-yl)oxy]-3-pyridinamine2×

Product 1

HCID 67966820HCID 67966820, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

6-[(3-ethyl-1,2-benzisoxazol-4-yl)oxy]-3-pyridinamine (Intermediate 33) was dissolved in DMF (0.5 mL) and added to a mixture of (2R)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)butanoic acid (7.7 mg, 0.038 mmol), DIPEA (0.008 mL, 0.047 mmol) and HATU (14.4 mg, 0.038 mmol) in 1 ml of DMF. The reaction mixture was then stirred at 50° C. for 2 hours. After the removal of DMF, water was added and the mixture was extracted with ethyl acetate. The gathered organic layers were dried over sodium sulphate, filtered and evaporated. The residue was then charged on a silica gel column (Biotage SP1 system) and eluted with Cyhexane/EtOAc (from all 10/0 to 7/3, then 7/3) to afford the title compound (4.4 mg).

Workup

  1. customAfter the removal of DMF, water
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe gathered organic layers were dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. additionThe residue was then charged on a silica gel column (Biotage SP1 system)
  8. washeluted with Cyhexane/EtOAc (from all 10/0 to 7/3

Sources & evidence

ORD record
ord-cfc3c38be1704db3950ed7ead1329242
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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