Diisopropylethylamine → HCID 59290365, compound

HRID 909948Notes

Reaction equation

HRID 909948 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]2[CH:9]=[C:10]([CH:19]=[CH:20][CH:21]=2)[CH2:11][CH2:12][O:13][CH2:14][CH2:15][C:16]([OH:18])=O)[CH:4]=[N:3]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.[CH3:55][O:56][CH:57]([O:66][CH3:67])[CH2:58][NH:59][CH:60]1[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]1>CN(C=O)C>[CH:60]1([N:59]([CH2:58][CH:57]([O:66][CH3:67])[O:56][CH3:55])[C:16](=[O:18])[CH2:15][CH2:14][O:13][CH2:12][CH2:11][C:10]2[CH:19]=[CH:20][CH:21]=[C:8]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[C:6]=3[CH3:7])[CH:9]=2)[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 3024915N-(2,2-dimethoxyethyl)cyclohexanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59290392HCID 59290392, compound

Product 1

HCID 59290365HCID 59290365, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(3-(1,5-dimethyl-1H-pyrazol-4-yl)phenethoxy)propanoic acid [Example 37 Step ii)] (0.3 g) and DIPEA (0.545 mL) in DMF (4 mL) was added HATU (0.475 g) and the mixture was stirred at ambient temperature for 10 min. To this solution was added N-(2,2-dimethoxyethyl)cyclohexanamine (0.214 g) and the reaction mixture was stirred at ambient temperature for 2.5 h. The reaction mixture was poured onto water and extracted with ethyl acetate (2×100 mL). The organics were washed well with water, then brine and dried over anhydrous sodium sulfate, filtered and evaporated. The crude product was purified by flash silica chromatography, elution gradient 20-70% ethyl acetate in isohexane to afford the titled compound (0.185 g) as an oil. MS [M+H-MeOH]+=426 (MultiMode+) 1H NMR (400 MHz, CDCl3) δ 7.54 (s, 1H), 7.33-7.27 (m, 1H), 7.22-7.17 (m, 2H), 7.12 (d, 1H), 3.84 (s, 3H), 3.79 (dt, 2H), 3.70 (dt, 2H), 3.40 (s, 6H), 3.37 (d, 1H), 3.30 (d, 1H), 2.94-2.88 (m, 2H), 2.74-2.65 (m, 2H), 2.38 (s, 3H), 1.86-1.73 (m, 2H), 1.73-1.59 (m, 3H), 1.53-1.19 (m, 5H), 1.14-1.02 (m, 1H).

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 2.5 h
  2. additionThe reaction mixture was poured onto water
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. washThe organics were washed well with water
  5. dry with materialbrine and dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by flash silica chromatography, elution gradient 20-70% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-44ecb175adb94de2ae5371149e3b5a5a
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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