Diisopropylethylamine → HCID 69673245, compound

HRID 2283244Notes

Reaction equation

HRID 2283244 reaction equation
C[C:2]1[N:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([C:14](O)=[O:15])[C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.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.[NH2:56][CH:57]([CH2:62][OH:63])[C:58]([O:60][CH3:61])=[O:59]>CN(C=O)C>[C:8]1([C:5]2[N:6]=[N:7][CH:2]=[C:3]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:4]=2[C:14]([NH:56][CH:57]([CH2:62][OH:63])[C:58]([O:60][CH3:61])=[O:59])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 416960Methyl DL-serinateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69673498HCID 69673498, compound

Product 1

HCID 69673245HCID 69673245, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The solution of compound 6 (50 mg, 1.81 mmol) in DMF (0.5 mL), DIPEA (93 mg, 0.72 mmol), HATU (138 mg, 0.36 mmol) were sequentially added and stirred for 10 min at rt. Then methyl 2-amino-3-hydroxypropanoate (84 mg, 0.54 mmol) was added and stirred overnight at rt. Reaction was quenched by addition of ice cold water. The precipitated solid was filtered, washed with hexane, dried over anhydrous Na2SO4 and azeotroped with toluene to furnish methyl 2-(3,5-diphenylpyridazine-4-carboxamido)-3-hydroxypropanoate (20 mg, 29%) as an off white solid.

Workup

  1. stirringstirred overnight at rt
  2. customReaction
  3. customwas quenched by addition of ice cold water
  4. filtrationThe precipitated solid was filtered
  5. washwashed with hexane
  6. dry with materialdried over anhydrous Na2SO4
  7. customazeotroped with toluene

Sources & evidence

ORD record
ord-7f6c3924503b46549ae3c3e3ed4f94c0
Source dataset
uspto-grants-2015_09
Patent number
US09145372B2

Reaction notes

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