Diisopropylethylamine → HCID 131735497, compound

HRID 520325Notes

Reaction equation

HRID 520325 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[C:11]([C:17]([OH:19])=O)=[N:12][CH:13]=[CH:14][C:15]=1[Cl:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:20]([C:24]1[CH:25]=[C:26]([NH2:31])[C:27]([NH2:30])=[CH:28][CH:29]=1)([CH3:23])([CH3:22])[CH3:21].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[NH2:31][C:26]1[CH:25]=[C:24]([C:20]([CH3:22])([CH3:21])[CH3:23])[CH:29]=[CH:28][C:27]=1[NH:30][C:17](=[O:19])[C:11]1[C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])=[C:15]([Cl:16])[CH:14]=[CH:13][N:12]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 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 131735495HCID 131735495, compound

Product 1

HCID 131735497HCID 131735497, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
19 °C

Procedure

A mixture of 160e (20 g, 66 mmol), 4-(tert-butyl)benzene-1,2-diamine 160f (10.8 g, 66 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (30 g, 79 mmol) and diisopropylethylamine (17 g, 132 mmol) in N,N-dimethylformamide (1000 mL) was stirred at 19° C. for 12 h. See FIG. 5. TLC (petroleum ether:ethyl acetate=1:1) showed that the starting material was completely consumed. The mixture was diluted with water (1000 mL) and extracted with EtOAc (1000 mL×2). The combined organic layers were washed with brine (500 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with petroleum ether:ethyl acetate=1:1) to afford N-(2-amino-4-(tert-butyl)phenyl)-3-(((tert-butyldimethylsilyl)oxy)methyl)-4-chloropicolinamide 160g (20 g, 67%) as a yellow solid.

Workup

  1. customwas completely consumed
  2. additionThe mixture was diluted with water (1000 mL)
  3. extractionextracted with EtOAc (1000 mL×2)
  4. washThe combined organic layers were washed with brine (500 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (eluting with petroleum ether:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-bab2b2a92c1c477bb5c55e6e523eba1d
Source dataset
uspto-grants-2016_05
Patent number
US09326985B2

Reaction notes

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