Diisopropylethylamine → HCID 53629672, compound

HRID 1175951Notes

Reaction equation

HRID 1175951 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]([O:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:15]=1)[C:10]([OH:12])=O)[CH3:5].[CH3:24][N:25]1[C:29]([CH3:30])=[CH:28][C:27]([NH2:31])=[N:26]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>CN(C=O)C>[CH3:24][N:25]1[C:29]([CH3:30])=[CH:28][C:27]([NH:31][C:10](=[O:12])[C:9]2[CH:13]=[C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:15]=[C:7]([O:6][C@@H:4]([CH3:5])[CH2:3][O:2][CH3:1])[CH:8]=2)=[N:26]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 70177471,5-dimethyl-1H-pyrazol-3-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59127150Benzoic acid, 3-[(1S)-2-methoxy-1-methylethoxy]-5-(phenylmethoxy)-

Product 1

HCID 53629672HCID 53629672, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-[(1S)-2-methoxy-(1-methylethyl)oxy]-5-{[phenylmethyl]oxy}benzoic acid (4.11 mmol) in DMF (10 mL) was treated with the 1,5-dimethyl-1H-pyrazol-3-ylamine (4.52 mmol), DIPEA (5.93 mmol) and HATU (3.85 mmol) and stirred at RT overnight, under an argon atmosphere. The mixture was poured onto water (100 mL) and extracted with ethyl acetate (3×100 mL). The organic layer was washed with brine (20 mL) and evaporated in vacuo before chromatography on silica, eluting with 20-80% ethyl acetate in isohexane, to afford the desired compound as a yellow oil (1.05 g).

Workup

  1. additionThe mixture was poured onto water (100 mL)
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe organic layer was washed with brine (20 mL)
  4. customevaporated in vacuo before chromatography on silica
  5. washeluting with 20-80% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-bb51ca2692e441f6bddf7997c17f6dd0
Source dataset
uspto-grants-2010_11
Patent number
US07842694B2

Reaction notes

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