Diisopropylethylamine → HCID 117680433, compound

HRID 332705Notes

Reaction equation

HRID 332705 reaction equation
[C:1]1([CH:7]([NH:25][C:26]([O:28][C@@H:29]2[CH:34]3[CH2:35][CH2:36][N:31]([CH2:32][CH2:33]3)[CH2:30]2)=[O:27])[C:8]2[CH:9]=[C:10]([CH:22]=[CH:23][CH:24]=2)[O:11][CH2:12][C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[NH2:70][CH2:71][CH2:72][CH:73]([O:77][CH2:78][CH3:79])[O:74][CH2:75][CH3:76]>CN(C=O)C.C(OCC)(=O)C>[N:31]12[CH2:32][CH2:33][CH:34]([CH2:35][CH2:36]1)[C@@H:29]([O:28][C:26](=[O:27])[NH:25][CH:7]([C:8]1[CH:24]=[CH:23][CH:22]=[C:10]([O:11][CH2:12][C:13]3[CH:21]=[CH:20][C:16]([C:17](=[O:18])[NH:70][CH2:71][CH2:72][CH:73]([O:77][CH2:78][CH3:79])[O:74][CH2:75][CH3:76])=[CH:15][CH:14]=3)[CH:9]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:30]2

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5210291-Amino-3,3-diethoxypropaneHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71093111HCID 71093111, compound

Product 1

HCID 117680433HCID 117680433, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-((3-(phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)-methyl)phenoxy)methyl)benzoic acid (0.300 g, 0.57 mmol) in DMF (2.5 mL), was added HATU (0.262 g, 0.69 mmol) and diisopropylethylamine (0.250 mL, 1.43 mmol), and the reaction mixture was stirred at room temperature for 30 minutes. 1-Amino-3,3-diethoxypropane (0.139 mL, 0.86 mmol) was added, and the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and washed sequentially with saturated sodium hydrogen carbonate and brine (×2). The organic phase was dried wih anhydrous sodium sulfate, and filtered, and the solvent was evaporated at reduced pressure. The crude material was purified by silica gel chromatography eluting with 100% iso-hexane to 100% ethyl acetate in iso-hexane to afford the title compound (0.347 g, 99%), which was used directly in the next step.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 18 hours
  2. washwashed sequentially with saturated sodium hydrogen carbonate and brine (×2)
  3. dry with materialThe organic phase was dried wih anhydrous sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated at reduced pressure
  6. customThe crude material was purified by silica gel chromatography
  7. washeluting with 100% iso-hexane to 100% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-9b0b63ab59cd4b34874a8e1b03a7ccda
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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