4-Tert-butylbenzene-1,2-diamine → HCID 86699083, compound

HRID 1424176Notes

Reaction equation

HRID 1424176 reaction equation
[Si]([N:8]1[C:11](=[O:12])[C@H:10]([CH2:13][CH3:14])[C@H:9]1[C:15](O)=O)(C(C)(C)C)(C)C.F[P-](F)(F)(F)(F)F.C[N+:26](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.[C:42]([C:46]1[CH:47]=[C:48]([NH2:53])[C:49]([NH2:52])=[CH:50][CH:51]=1)([CH3:45])([CH3:44])[CH3:43]>CN(C)C=O.O>[NH2:26][C@H:9]([C:15]1[NH:53][C:48]2[CH:47]=[C:46]([C:42]([CH3:45])([CH3:43])[CH3:44])[CH:51]=[CH:50][C:49]=2[N:52]=1)[C@@H:10]([CH2:13][CH3:14])[C:11]([NH2:8])=[O:12]

Participants

6

Reactant 3

HCID 4327084-Tert-butylbenzene-1,2-diamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 14543850HCID 14543850, compound

Product 1

HCID 86699083HCID 86699083, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(2S,3R)-1-(tert-Butyldimethylsilyl)-3-ethyl-4-oxoazetidine-2-carboxylic acid (Tetrahedron, 46(7), 2255-62; 1990, 100 mg, 0.388 mmol) was dissolved in N,N-dimethylformamide (2 mL) and N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (418 mg, 1.10 mmol) was added. The reaction mixture was stirred for 20 minutes then 4-(tert-butyl)benzene-1,2-diamine (165 mg, 1.00 mmol) was added and the reaction mixture stirred at ambient temperature for 18 hours. The reaction mixture was diluted with water and extracted three times with ethyl ether. The combined organic phase was dried over anhydrous magnesium sulfate, filtered and the solvent removed in-vacuo. The residue was purified by silica gel column chromatography eluting with 0-100% ethyl acetate in hexanes to afford the amide as a mixture of isomers.

Workup

  1. stirringthe reaction mixture stirred at ambient temperature for 18 hours
  2. extractionextracted three times with ethyl ether
  3. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed in-vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with 0-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-602efb28eebd40e4aa9e2f137144ce09
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

Loading…